Oligosaccharide compositions for use as animal feed and methods of producing thereof

ABSTRACT

Described herein are methods of producing animal feed made up of oligosaccharide compositions, as well as methods of producing such oligosaccharide compositions and animal feed compositions, and methods of using such animal feed compositions to enhance animal growth.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to U.S. Provisional Patent ApplicationsNos., 62/108,037 filed Jan. 26, 2015, 62/216,945 filed Sep. 10, 2015,62/216,952 filed Sep. 10, 2015, 62/255,341 filed Nov. 13, 2015, and62/255,343 filed Nov. 13, 2015, the disclosures of which are herebyincorporated by reference in their entireties.

FIELD

The present disclosure relates generally to feed materials suitable foranimal consumption, and more specifically to animal feed that includeoligosaccharide compositions, methods of increasing animal growth byfeeding an animal such oligosaccharide compositions, and methods ofproducing such oligosaccharide compositions.

BACKGROUND

As the global human population rises, the demand for animal productsalso grows. Meeting this demand requires raising increasingly moreanimals while maximizing utilization of limited resources. Furthermore,animals raised under commercial conditions often face challenges, suchas living in close proximity to many other animals. These conditions canhave a negative impact on animal health by, for example, facilitatingthe spread of disease, lowering overall growth performance, andincreasing stress-induced mortality.

Additives have been developed for use in animal feed to counteract thesechallenges. For example, antibiotics are often used to promote healthand increase weight gain in poultry, swine, fish, and other productionanimals. However, concerns about the effect of antibiotic additives onhuman health and development of drug-resistant bacteria have led to anincreased demand in the consumer market for animals raised withoutantibiotic additives.

Oligosaccharide additives can also be used to improve animal health,growth rate, and the efficient conversion of feed by the animal. Theimpact of oligosaccharides on animal growth and well-being depends ontheir physiochemical properties, which can have physiological andmorphological effects on the digestive tract. For example, factorsincluding viscosity, monomer composition, and molecular mass can alterintestinal transit time, intestinal mucosa, nutrient absorption, andhormonal regulation.

Methods of producing such additives known in the art include theenzymatic hydrolysis or acid hydrolysis of longer chain oligosaccharidesand polysaccharides to produce oligosaccharide additives. Enzymaticmethods can generate degradation side products that cause metabolicproblems when consumed by poultry, swine and livestock. Additionally, itcan sometimes be difficult to control the physiochemical properties ofoligosaccharides produced using acid hydrolysis.

Thus, there is a need in the art for animal feed additives, that can beprovided at a lower inclusion rate, while maintaining or increasinganimal weight. There is also a need in the art for methods of producingsuch animal feed additives.

BRIEF SUMMARY

The present application addresses this need in the art by providingoligosaccharide compositions suitable for use in animal feedcompositions, and methods for producing oligosaccharide compositionssuitable for use in animal feed compositions. In one aspect, provided isa method of producing an animal feed composition, by: combining feedsugar with a catalyst to form a reaction mixture; producing anoligosaccharide composition from at least a portion of the reactionmixture; and combining the oligosaccharide composition with a base feedto produce an animal feed composition.

In embodiments of the foregoing, the catalyst is a polymeric catalystthat includes acidic monomers and ionic monomers connected to form apolymeric backbone; or the catalyst is a solid-supported catalyst thatincludes a solid support, acidic moieties attached to the solid support,and ionic moieties attached to the solid support.

In some variations, the animal feed composition is poultry feed. Inother variations, the animal feed composition is swine feed. In certainvariations, the animal feed composition is in liquid or solid form.

In another aspect, provided is a method of increasing weight gain in ananimal, by: feeding to the animal an animal feed composition producedaccording to any of the methods described herein, wherein the animalfeed composition is fed to the animal at an inclusion rate of less than1,000 mg/kg, or less than 500 mg/kg. In yet another aspect, provided isa method of improving weight gain and reducing feed conversion ratio ofan animal, by: feeding to the animal an animal feed composition producedaccording to any of the methods described herein. In some variations ofthe foregoing aspects, the animal is a monogastric species. In certainvariations of the foregoing aspects, the animal is a chicken. In othervariations of the foregoing aspects, the animal is a pig. In yet othervariations of the foregoing aspects, the animal is a fish. In othervariations of the foregoing aspects, the animal is a ruminant species,for example a cow.

Provided is also an animal feed composition produced according to any ofthe methods described herein.

In one aspect, provided herein is an animal feed composition whichincludes (i) a base feed, and (ii) an oligosaccharide composition;wherein the oligosaccharide composition has a glycosidic bond typedistribution of at least 10 mol % α-(1,3) glycosidic linkages, and atleast 10 mol % β-(1,3) glycosidic linkages; and wherein at least 10 drywt % of the oligosaccharide composition has a degree of polymerizationof at least 3.

In another aspect, provided herein is an animal feed composition whichincludes (i) a base feed, and (ii) an oligosaccharide composition,wherein the oligosaccharide composition has a glycosidic bond typedistribution of less than 9 mol % α-(1,4) glycosidic linkages and lessthan 19 mol % α-(1,6) glycosidic linkages; and wherein at least 10 drywt % of the oligosaccharide composition has a degree of polymerizationof at least 3.

In certain embodiments, the oligosaccharidec composition has aglycosidic bond type distribution of at least 15 mol % β-(1,2)glycosidic linkages. In some embodiments, at least 50 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3. In some embodiments, the base feed is poultry feed.

In other aspects, provided herein is an animal feed pre-mix, whichincludes (i) a carrier material, and (ii) an oligosaccharidecomposition, wherein the oligosaccharide composition has a glycosidicbond type distribution of at least 1 mol % α-(1,3) glycosidic linkagesand at least 1 mol % β-(1,3) glycosidic linkages; and wherein at least10 dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In another aspect, provided herein is an animal feed pre-mix, whichincludes (i) a carrier material, and (ii) an oligosaccharidecomposition, wherein the oligosaccharide composition has a glycosidicbond type distribution of less than 20 mol % α-(1,4) glycosidic linkagesand less than 30 mol % α-(1,6) glycosidic linkages; and wherein at least10 dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In certain embodiments, the oligosaccharide composition has a glycosidicbond type distribution of at least 15 mol % β-(1,6) glycosidic linkages.In some embodiments, the animal feed pre-mix reduces feed conversionratio (FCR) by between 1 to 10% when fed to an animal as compared to ananimal fed a feed composition without the oligosaccharide composition.

In yet another aspect, provided herein is a method of enhancing growthof poultry by providing feed to poultry, wherein the feed includes (i) abase feed, and (ii) an oligosaccharide composition, wherein theoligosaccharide composition has a glycosidic bond type distribution ofat least 1 mol % α-(1,3) glycosidic linkages and at least 1 mol %β-(1,3) glycosidic linkages; and wherein at least 10 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3; and enhancing growth in the poultry.

In still another aspect, provided herein is a method of decreasing feedconversion ratio of feed provided to poultry by providing feed topoultry, wherein the feed includes (i) a base feed, and (ii) anoligosaccharide composition, wherein the oligosaccharide composition hasa glycosidic bond type distribution of at least 1 mol % α-(1,3)glycosidic linkages and at least 1 mol % β-(1,3) glycosidic linkages;wherein at least 10 dry wt % of the oligosaccharide composition has adegree of polymerization of at least 3; and decreasing the feedconversion ratio (FCR) of feed provided to the poultry.

In some embodiments, the oligosaccharide composition has a bonddistribution of at least 15 mol % β-(1,6) glycosidic linkages. Incertain embodiments, the feed conversion ratio (FCR) is between 0 to 4%higher than the performance target minimum. In other embodiments, theanimal is poultry, and the poultry has an average daily weight gain, andwherein the average daily weight gain is at least 2% greater than theaverage daily weight gain of poultry provided feed without theoligosaccharide composition. In other embodiments, the animal is swine,and the swine has an average daily weight gain, and wherein the averagedaily weight gain is at least 2% greater than the average daily weightgain of swine provided feed without the oligosaccharide composition.

In yet another aspect, provided herein is a method of enhancing growthof an animal population, by feeding to the animal population an animalfeed, wherein the animal feed comprises an oligosaccharide compositionat an inclusion rate of less than 5,000 ppm wt % dry oligosaccharidecomposition per weight of animal feed; wherein the oligosaccharidecomposition has a glycosidic bond type distribution of at least 1 mol %α-(1,3) glycosidic linkages and at least 1 mol % β-(1,3) glycosidiclinkages; and wherein at least 10 dry wt % of the oligosaccharidecomposition has a degree of polymerization of at least 3; and enhancinggrowth of the animal population.

In some embodiments, the animal population is a poultry population. Insome embodiments, the animal population is a swine population.

DESCRIPTION OF THE FIGURES

The present application can be understood by reference to the followingdescription taken in conjunction with the accompanying figures.

FIG. 1 depicts an exemplary process to produce an oligosaccharidecomposition from sugars in the presence of a catalyst.

FIG. 2A illustrates a portion of a catalyst with a polymeric backboneand side chains.

FIG. 2B illustrates a portion of an exemplary catalyst, in which a sidechain with the acidic group is connected to the polymeric backbone by alinker and in which a side chain with the cationic group is connecteddirectly to the polymeric backbone.

FIG. 3 depicts a reaction scheme to prepare a dual-functionalizedcatalyst from an activated carbon support, in which the catalyst hasboth acidic and ionic moieties.

FIG. 4 illustrates a portion of a polymeric catalyst, in which themonomers are arranged in blocks of monomers, and the block of acidicmonomers alternates with the block of ionic monomers.

FIG. 5A illustrates a portion of a polymeric catalyst with cross-linkingwithin a given polymeric chain.

FIG. 5B illustrates a portion of a polymeric catalyst with cross-linkingwithin a given polymeric chain.

FIG. 6A illustrates a portion of a polymeric catalyst with cross-linkingbetween two polymeric chains.

FIG. 6B illustrates a portion of a polymeric catalyst with cross-linkingbetween two polymeric chains.

FIG. 6C illustrates a portion of a polymeric catalyst with cross-linkingbetween two polymeric chains.

FIG. 6D illustrates a portion of a polymeric catalyst with cross-linkingbetween two polymeric chains.

FIG. 7 illustrates a portion of a polymeric catalyst with a polyethylenebackbone.

FIG. 8 illustrates a portion of a polymeric catalyst with apolyvinylalcohol backbone.

FIG. 9 illustrates a portion of a polymeric catalyst, in which themonomers are randomly arranged in an alternating sequence.

FIG. 10 illustrates two side chains in a polymeric catalyst, in whichthere are three carbon atoms between the side chain with theBronsted-Lowry acid and the side chain with the cationic group.

FIG. 11 illustrates two side chains in a polymeric catalyst, in whichthere are zero carbons between the side chain with the Bronsted-Lowryacid and the side chain with the cationic group.

FIG. 12 illustrates a portion of a polymeric catalyst with an ionomericbackbone.

FIG. 13 is a graph depicting the mean weight gain of poultry after thefirst 14 days of a diet supplemented with an oligosaccharide additiveprepared with a catalyst including acidic moieties and ionic moieties,additives prepared by other methods, or no additive.

FIG. 14 is a graph depicting the mean weight gain of poultry following35 days of a diet supplemented with an oligosaccharide additive preparedwith a catalyst including acidic moieties and ionic moieties, additivesprepared by other methods, or no additive.

FIG. 15 is a graph depicting the feed conversion ratio (FCR) of poultryfollowing 35 days of a diet supplemented with an oligosaccharideadditive prepared with a catalyst including acidic moieties and ionicmoieties, additives prepared by other methods, or no additive.

FIG. 16 is a graph depicting the short chain fatty acid (SCFA)concentration in the caecum from a sample of birds in each group ofpoultry following 35 days of a diet supplemented with an oligosaccharideadditive prepared with a catalyst including acidic moieties and ionicmoieties, additives prepared by other methods, or no additive.

FIG. 17 is a graph depicting the butyric acid concentration in thecaecum from a sample of birds in each group of poultry following 35 daysof a diet supplemented with an oligosaccharide additive prepared with acatalyst including acidic moieties and ionic moieties, additivesprepared by other methods, or no additive.

FIG. 18 is a graph depicting the mean 0-35 day corrected feed conversionratios (cFCR) for populations of poultry as a function ofgluco-oligosaccharide inclusion rate.

FIG. 19 depicts an exemplary process to produce a functionalizedoligosaccharide composition, wherein a portion of an oligosaccharidecomprising pendant functional groups and bridging functional groups isshown.

FIG. 20 is a graph that depicts 0-42 day Body Weight Gain (BWG) versusoligosaccharide dose, and a linear regression analysis in the absence(ABX Negatitve) and presence (ABX Positive) of antibiotic growthpromoters.

FIG. 21 is a graph that depicts 0-42 day Average Daily Gain (ADG) versusoligosaccharide dose and linear regression analysis in the absence (ABXNegatitve) and presence (ABX Positive) of antibiotic growth promoters.

FIG. 22 is a graph that depicts 0-42 day Average Daily Feed Intake(ADFI) versus oligosaccharide dose and linear regression analysis in theabsence (ABX Negatitve) and presence (ABX Positive) of antibiotic growthpromoters.

FIG. 23 is a graph that depicts 0-42 day Feed Conversion Ratio (FCR)versus oligosaccharide dose and linear regression analysis in theabsence (ABX Negatitve) and presence (ABX Positive) of antibiotic growthpromoters.

DETAILED DESCRIPTION

The following description sets forth exemplary methods, parameters andthe like. It should be recognized, however, that such description is notintended as a limitation on the scope of the present disclosure but isinstead provided as a description of exemplary embodiments.

Provided herein are oligosaccharide compositions suitable for use inanimal feed compositions. In some aspects, the oligosaccharidecompositions described herein may be fed directly to animals, or may beincorporated into animal feed to form an animal feed composition. Theoligosaccharide compositions provided herein may be fed to an animal atan inclusion rate lower than what is typically used in the art, andeither maintain or increase the weight of the animal. Theoligosaccharide compositions provided herein fed to animals may enhanceanimal growth, including, for example, increasing weight gain,decreasing the food conversion ratio (FCR), increasing digestibility ofprovided feed, increasing released nutrients from provided feed,reducing mortality rate, and/or increasing animal uniformity.

Moreover, the oligosaccharide compositions provided herein fed toanimals can help the animals get closer to their genetic potential andoptimum growth, by helping the animal grow under conditions that do nototherwise allow it to reach optimal growth.

The oligosaccharide compositions, the animal feed compositions, the useof such animal feed compositions, and the methods of producing sucholigosaccharide compositions and animal feeds are described hereinfurther detail below. For example, the animals may suffer from a diseaseor disorder, or may be raised in a stressed environment (due to, forexample, pathogenic stress, heat stress, humidity stress, crowding, orother social interaction effects, such as difficulty accessing feed ordrinking water.

The oligosaccharide compositions, and their uses and methods of makingthereof, are described in further detail below.

Oligosaccharide Compositions

In some aspects, provided herein are oligosaccharide compositionssuitable for use as, or incorporation into, animal feed. As used herein,“animal feed” generally refers to feed suitable for non-humanconsumption. For example, poultry feed refers to feed suitable forpoultry consumption; swine feed refers to feed suitable for swineconsumption. The oligosaccharide compositions produced according to themethods described herein and the properties of such compositions mayvary, depending on the type of sugars as well as the reaction conditionsused. The oligosaccharide compositions may be characterized based on thetype of oligosaccharides present, degree of polymerization, glasstransition temperature, hygroscopicity, and glycosidic bond typedistribution.

Types of Oligosaccharides

In some embodiments, the oligosaccharide compositions include anoligosaccharide comprising one type of sugar monomer. For example, insome embodiments, the oligosaccharide compositions may include agluco-oligosaccharide, a galacto-oligosaccharide, afructo-oligosaccharide, a manno-oligosaccharide, anarabino-oligosaccharide, or a xylo-oligosaccharide, or any combinationsthereof. In some embodiments, the oligosaccharide compositions includean oligosaccharide comprising two different types of sugar monomers. Forexample, in some embodiments, the oligosaccharide compositions mayinclude a gluco-galacto-oligosaccharide, a gluco-fructo-oligosaccharide,a gluco-manno-oligosaccharide, a gluco-arabino-oligosaccharide, agluco-xylo-oligosaccharide, a galacto-fructo-oligosaccharide, agalacto-manno-oligosaccharide, a galacto-arabino-oligosaccharide, agalacto-xylo-oligosaccharide, a fructo-manno-oligosaccharide, afructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, amanno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, or anarabino-xylo-oligosaccharide, or any combinations thereof. In someembodiments, the oligosaccharide compositions include an oligosaccharidecomprising more than two different types of sugar monomers. In somevariations, the oligosaccharide compositions include an oligosaccharidecomprising 3, 4, 5, 6, 7, 8, 9, or 10 different types of sugar monomers.For example, in certain variations the oligosaccharide compositionsinclude an oligosaccharide comprising agalacto-arabino-xylo-oligosaccharide, afructo-galacto-xylo-oligosaccharide, aarabino-fructo-manno-xylo-oligosaccharide, agluco-fructo-galacto-arabino-oligosaccharide, afructo-gluco-arabino-manno-xylo oligosaccharide, or agluco-galacto-fructo-manno-arabino-xylo-oligosaccharide.

In some embodiments, the oligosaccharide compositions include agluco-oligosaccharide, a manno-oligosaccharide, agluco-galacto-oligosaccharide, a xylo-oligosaccharide, anarabino-galacto-oligosaccharide, a gluco-galacto-xylo-oligosaccharide,an arabino-xylo-oligosaccharide, a gluco-xylo-oligosaccharide, or axylo-gluco-galacto-oligosaccharide, or any combinations thereof. In onevariation, the oligosaccharide compositions include agluco-galacto-oligosaccharide. In another variation, the oligosaccharidecompositions include a xylo-gluco-galacto-oligosaccharide.

As used herein, “oligosaccharide” refers to a compound containing two ormore monosaccharide units linked by glycosidic bonds.

In some embodiments, at least one of the two or more monosaccharideunits is a sugar in L-form. In other embodiments, at least one of thetwo or more monosaccharides is a sugar in D-form. In yet otherembodiments, the two or more monosaccharide units are sugars in L- orD-form according to their naturally-abundant form (e.g., D-glucose,D-xylose, L-arabinose).

In some embodiments, the oligosaccharide composition comprises a mixtureof L- and D-forms of monosaccharide units, e.g. of a ratio, such as:1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:12, 1:14, 1:16,1:18, 1:20, 1:25, 1:30, 1:35, 1:40, 1:45, 1:50, 1:55, 1:60, 1:65, 1:70,1:75, 1:80, 1:85, 1:90, 1:100, 1:150 L- to D-forms or D- to L-forms. Insome embodiments, the oligosaccharide comprises monosaccharide unitswith substantially all L- or D-forms of glycan units, optionallycomprising 1%, 2%, 3%, 4% 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%,15%, 16%, 17%, 18%, 19%, or 20% of the respective other form.

As used herein, “gluco-oligosaccharide” refers to a compound containingtwo or more glucose monosaccharide units linked by glycosidic bonds.Similarly, “galacto-oligosaccharide” refers to a compound containing twoor more galactose monosaccharide units linked by glycosidic bonds.

As used herein, “gluco-galacto-oligosaccharide” refers to a compoundcontaining one or more glucose monosaccharide units linked by glycosidicbonds, and one or more galactose monosaccharide units linked byglycosidic bonds. In some embodiments, the ratio of glucose to galactoseon a dry mass basis is between 10:1 glucose to galactose to 0.1:1glucose to galactose, 5:1 glucose to galactose to 0.2:1 glucose togalactose, 2:1 glucose to galactose to 0.5:1 glucose to galactose. Inone embodiment, the ratio of glucose to galactose is 1:1.

In one variation, the oligosaccharide composition is a longoligosaccharide composition, while in another variation theoligosaccharide composition is a short oligosaccharide composition. Asused herein, the term “long oligosaccharide composition” refers to anoligosaccharide composition with an average degree of polymerization(DP) of about 8, about 9, about 10, about 11, about 12, about 13, about14, about 15, about 16, about 17, about 18, about 19, or about 20. Asused herein, the term “short oligosaccharide composition” refers tooligosaccharide composition with an average DP of about 2, about 3,about 4, about 5, about 6, or about 7.

Functionalized Oligosaccharide Compositions

In some variations, the oligosaccharide compositions described hereinare functionalized oligosaccharide compositions. Functionalizedoligosaccharide compositions may be produced by, for example, combiningone or more sugars (e.g., feed sugars) with one or more functionalizingcompounds in the presence of a catalyst, including, for example,polymeric catalysts and solid-supported catalysts as described in WO2012/118767 and WO 2014/031956. In certain variations, a functionalizedoligosaccharide is a compound comprising two or more monosaccharideunits linked by glycosidic bonds in which one or more hydroxyl groups inthe monosaccharide units are independently replaced by a functionalizingcompound, or comprise a linkage to a functionalizing compound. Thefunctionalizing compound may be a compound that can attach to theoligosaccharide through an ether, ester, oxygen-sulfur, amine, oroxygen-phosphorous bond, and which does not contain a monosaccharideunit.

Functionalizing Compounds

In certain variations, the functionalizing compound comprises one ormore functional groups independently selected from amine, hydroxyl,carboxylic acid, sulfur trioxide, sulfate, and phosphate. In somevariations, one or more functionalizing compounds are independentlyselected from the group consisting of amines, alcohols, carboxylicacids, sulfates, phosphates, or sulfur oxides.

In some variations, the functionalizing compound has one or morehydroxyl groups. In some variations, the functionalizing compound withone or more hydroxyl groups is an alcohol. Such alcohols may include,for example, alkanols and sugar alcohols.

In certain variations, the functionalizing compound is an alkanol withone hydroxyl group. For example, in some variations, the functionalizingcompound is selected from ethanol, propanol, butanol, pentanol, andhexanol. In other variations, the functionalizing compound has two ormore hydroxyl groups. For example, in some variations, thefunctionalizing compound is selected from propanediol, butanediol, andpentanediol.

For example, in one variation, one or more sugars (e.g., feed sugars)may be combined with a sugar alcohol in the presence of a polymericcatalyst to produce a functionalized oligosaccharide composition.Suitable sugar alcohols may include, for example, sorbitol (also knownas glucitol), xylitol, lacitol, arabinatol (also known as arabitol),glycerol, erythritol, mannitol, galacitol, fucitol, iditol, inositol, orvolemitol, or any combinations thereof.

In another variation, wherein the functionalizing compound comprises ahydroxyl group, the functionalizing compound may become attached to themonosaccharide unit through an ether bond. The oxygen of the ether bondmay be derived from the monosaccharide unit, or from the functionalizingcompound.

In yet other variations, the functionalizing compound comprises one ormore carboxylic acid functional groups. For example, in some variations,the functionalizing compound is selected from lactic acid, acetic acid,citric acid, pyruvic acid, succinic acid, glutamic acid, itaconic acid,malic acid, maleic acid, propionic acid, butanoic acid, pentanoic acid,hexanoic acid, adipic acid, isobutyric acid, formic acid, levulinicacid, valeric acid, and isovaleric acid. In other variations, thefunctionalizing compound is a sugar acid. For example, in oneembodiment, the functionalizing compound is gluconic acid. In certainvariations, wherein the functionalizing compound comprises a carboxylicacid group, the functionalizing compound may become attached to themonosaccharide unit through an ester bond. The non-carbonyl oxygen ofthe ester bond may be derived from the monosaccharide unit, or from thefunctionalizing compound.

In still other variations, the functionalizing compound comprises one ormore amine groups. For example, in some variations, the functionalizingcompound is an amino acid, while in other variations the functionalizingcompound is an amino sugar. In one variation, the functionalizingcompound is selected from glutamic acid, aspartic acid, glucosamine andgalactosamine. In certain variations, wherein the functionalizingcompound comprises an amine group, the functionalizing compound maybecome attached to the monosaccharide unit through an amine bond.

In yet other variations, the functionalizing compound comprises a sulfurtrioxide group or a sulfate group. For example, in one variation, thefunctionalizing compound is dimethylformamide sulfur trioxide complex.In another variation, the functionalizing compound is sulfate. In oneembodiment, the sulfate is produced in situ, from, for example, sulfurtrioxide. In certain variations wherein the functionalizing compoundcomprises a sulfur trioxide or sulfate group, the functionalizingcompound may become attached to the monosaccharide unit through anoxygen-sulfur bond.

In still other variations, the functionalizing compound comprises aphosphate group. In certain variations wherein the functionalizingcompound comprises a phosphate group, the functionalizing compound maybecome attached to the monosaccharide unit through an oxygen-phosphorousbond.

It should be understood that the functionalizing compounds describedherein may contain a combination of functional groups. For example, thefunctionalizing compound may comprise one or more hydroxyl groups andone or more amine groups (for example, amino sugars). In otherembodiments, the functionalizing compound may comprise one or morehydroxyl groups and one or more carboxylic acid groups (for example,sugar acids). In yet other embodiments, the functionalizing compound maycomprise one or more amine groups and one or more carboxylic acid groups(for example, amino acids). In still other embodiments, thefunctionalizing compound comprises one or more additional functionalgroups, such as esters, amides, and/or ethers. For example, in certainembodiments, the functionalizing compound is a sialic acid (for example,N-acetylneuraminic acid, 2-keto-3-deoxynonic acid, and other N- orO-substituted derivatives of neuraminic acid).

It should further be understood that a functionalizing compound maybelong to one or more of the groups described above. For example, aglutamic acid is both an amine and a carboxylic acid, and a gluconicacid is both a carboxylic acid and an alcohol.

In some variations, the functionalizing compound forms a pendant groupon the oligosaccharide. In other variations, the functionalizingcompound forms a bridging group between an oligomer backbone and asecond oligomer backbone; wherein each oligomer backbone independentlycomprises two or more monosaccharide units linked by glycosidic bonds;and the functionalizing compound is attached to both backbones. In othervariations, the functionalizing compound forms a bridging group betweenan oligomer backbone and a monosaccharide; wherein the oligomer backbonecomprises two or more monosaccharide units linked by glycosidic bonds;and the functionalizing compound is attached to the backbone and themonosaccharide.

Pendant Functional Groups

In certain variations, combining one or more sugars (e.g., feed sugars)and one or more functionalizing compounds in the presence of a catalyst,including polymeric catalysts and solid-supported catalysts as describedin WO 2012/118767 and WO 2014/031956, produces a functionalizedoligosaccharide composition. In certain embodiments, a functionalizingcompound is attached to a monosaccharide subunit as a pendant functionalgroup.

A pendant functional group may include a functionalization compoundattached to one monosaccharide unit, and not attached to any othermonosaccharide units. In some variations, the pendant functional groupis a single functionalization compound attached to one monosaccharideunit. For example, in one variation, the functionalizing compound isacetic acid, and the pendant functional group is acetate bonded to amonosaccharide through an ester linkage. In another variation, thefunctionalizing compound in propionic acid, and the pendant functionalgroup is propionate bonded to a monosaccharide through an ester linkage.In yet another variation, the functionalizing compound is butanoic acid,and the pendant functional group is butanoate bonded to a monosaccharidethrough an ester linkage. In other variations, a pendant functionalgroup is formed from linking multiple functionalization compoundstogether. For example, in some embodiments, the functionalizationcompound is glutamic acid, and the pendant functional group is a peptidechain of two, three, four, five, six, seven, or eight glutamic acidresidues, wherein the chain is attached to a monosaccharide through anester linkage. In other embodiments, the peptide chain is attached tothe monosaccharide through an amine linkage.

The pendant functional group may comprise a single linkage to themonosaccharide, or multiple linkages to the monosaccharide. For example,in one embodiment, the functionalization compound is ethanediol, and thependant functional group is ethyl connected to a monosaccharide throughtwo ether linkages.

Referring to FIG. 19 , process 1900 depicts an exemplary scheme toproduce an oligosaccharide containing different pendant functionalgroups. In process 1900, monosaccharides 1902 (represented symbolically)are combined with the functionalizing compound ethane diol 1904 in thepresence of catalyst 1906 to produce an oligosaccharide. Portion 1910 ofthe oligosaccharide is shown in FIG. 19 , wherein the monosaccharideslinked through glycosidic bonds are represented symbolically by circlesand lines. The oligosaccharide comprises three different pendantfunctional groups, as indicated by the labeled section. These pendantfunctional groups include a single functionalization compound attachedto a single monosaccharide unit through one linkage; twofunctionalization compounds linked together to form a pendant functionalgroup, wherein the pendant functional group is linked to a singlemonosaccharide unit through one linkage; and a single functionalizationcompound attached to a single monosaccharide unit through two linkages.It should be understood that while the functionalization compound usedin process 1900 is ethanediol, any of the functionalization compounds orcombinations thereof described herein may be used. It should be furtherunderstood that while a plurality of pendant functional groups ispresent in portion 1910 of the oligosaccharide, the number and type ofpendant functional groups may vary in other variations of process 1900.

It should be understood that any functionalization compounds may form apendant functional group. In some variations, the functionalizedoligosaccharide composition contains one or more pendant groups selectedfrom the group consisting of glucosamine, galactosamine, citric acid,succinic acid, glutamic acid, aspartic acid, glucuronic acid, butyricacid, itaconic acid, malic acid, maleic acid, propionic acid, butanoicacid, pentanoic acid, hexanoic acid, adipic acid, isobutyric acid,formic acid, levulinic acid, valeric acid, isovaleric acid, sorbitol,xylitol, arabitol, glycerol, erythritol, mannitol, galacitol, fucitol,iditol, inositol, volemitol, lacitol, ethanol, propanol, butanol,pentanol, hexanol, propanediol, butanediol, pentanediol, sulfate andphosphate.

Bridging Functional Groups

In certain variations, combining one or more sugars (e.g., feed sugars)and one or more functionalizing compounds in the presence of a catalyst,including polymeric catalysts and solid-supported catalysts as describedin WO 2012/118767 and WO 2014/031956, produces a functionalizedoligosaccharide comprising a bridging functional group.

Bridging functional groups may include a functionalization compoundattached to one monosaccharide unit and attached to at least oneadditional monosaccharide unit. The monosaccharide units mayindependently be monosaccharide units of the same oligosaccharidebackbone, monosaccharide units of separate oligosaccharide backbones, ormonosaccharide sugars that are not bonded to any additionalmonosaccharides. In some variations, the bridging functional compound isattached to one additional monosaccharide unit. In other variations, thebridging functional compound is attached to two or more additionalmonosaccharide units. For example, in some embodiments, the bridgingfunctional compound is attached to two, three, four, five, six, seven,or eight additional monosaccharide units. In some variations, thebridging functional group is formed by linking a singlefunctionalization compound to two monosaccharide units. For example, inone embodiment, the functionalization compound is glutamic acid, and thebridging functional group is a glutamate residue attached to onemonosaccharide unit through an ester bond, and an additionalmonosaccharide unit through an amine bond. In other embodiments, thebridging functionalization group is formed by linking multiplefunctionalization compound molecules to each other. For example, in oneembodiment, the functionalization compound is ethanediol, and thebridging functional group is a linear oligomer of four ethanediolmolecules attached to each other through ether bonds, the firstethanediol molecule in the oligomer is attached to one monosaccharideunit through an ether bond, and the fourth ethanediol molecule in theoligomer is attached to an additional monosaccharide unit through anether bond.

Referring again to FIG. 19 , portion 1910 of the oligosaccharideproduced according to process 1900 comprises three different bridgingfunctional groups, as indicated by the labeled section. These bridgingfunctional groups include a single functionalization compound attachedto a monosaccharide unit of an oligosaccharide through one linkage, andattached to a monosaccharide sugar through an additional linkage; asingle functionalization compound attached to two differentmonosaccharide units of the same oligosaccharide backbone; and twofunctionalization compounds linked together to form a bridgingfunctional group, wherein the bridging functional group is linked to onemonosaccharide unit through one linkage and to an additionalmonosaccharide unit through a second linkage. It should be understoodthat while the functionalization compound used in process 1900 isethanediol, any of the functionalization compounds or combinationsthereof described herein may be used. It should be further understoodthat while a plurality of bridging functional groups is present inportion 1910 of the oligosaccharide, the number and type of bridgingfunctional groups may vary in other variations of process 1900.

It should be understood that any functionalization compounds with two ormore functional groups able to form bonds with a monosaccharide may forma bridging functional group. For example, bridging functional groups maybe selected from polycarboxylic acids (such as succinic acid, itaconicacid, malic acid, maleic acid, and adipic acid), polyols (such assorbitol, xylitol, arabitol, glycerol, erythritol, mannitol, galacitol,fucitol, iditol, inositol, volemitol, and lacitol), and amino acids(such as glutamic acid). In some variations, the functionalizedoligosaccharide composition comprises one or more bridging groupsselected from the group consisting of glucosamine, galactosamine, lacticacid, acetic acid, citric acid, pyruvic acid, succinic acid, glutamicacid, aspartic acid, glucuronic acid, itaconic acid, malic acid, maleicacid, adipic acid, sorbitol, xylitol, arabitol, glycerol, erythritol,mannitol, galacitol, fucitol, iditol, inositol, volemitol, lacitol,propanediol, butanediol, pentanediol, sulfate and phosphate.

Functionalized oligosaccharide compositions comprising a mixture ofpendant functional groups and bridging functional groups may also beproduced using the methods described herein. For example, in certainembodiments, one or more sugars are combined with a polyol in thepresence of a catalyst, and a functionalized oligosaccharide compositionis produced wherein at least a portion of the composition comprisespendant polyol functional groups attached to oligosaccharides throughether linkages, and at least a portion comprises bridging polyolfunctional groups wherein each group is attached to a firstoligosaccharide through a first ether linkage and a secondoligosaccharide through a second ether linkage.

It should further be understood that the one or more functionalizationcompounds combined with the sugars, oligosaccharide composition, orcombination thereof may form bonds with other functionalizationcompounds, such that the functionalized oligosaccharide compositioncomprises monosaccharide units bonded to a first functionalizationcompound, wherein the first functionalization compound is bonded to asecond functionalization compound.

Degree of Polymerization

The oligosaccharide content of reaction products can be determined,e.g., by a combination of high performance liquid chromatography (HPLC)and spectrophotometric methods. For example, the average degree ofpolymerization (DP) for the oligosaccharides can be determined as thenumber average of species containing one, two, three, four, five, six,seven, eight, nine, ten to fifteen, and greater than fifteen,anhydrosugar monomer units.

In some embodiments, the oligosaccharide degree of polymerization (DP)distribution for the one or more oligosaccharides after combining theone or more sugars with the catalyst (e.g., at 2, 3, 4, 8, 12, 24, or 48hours after combining the one or more sugars with the catalyst) is:DP2=0%-40%, such as less than 40%, less than 30%, less than 20%, lessthan 10%, less than 5%, or less than 2%; or 10%-30% or 15%-25%;DP3=0%-20%, such as less than 15%, less than 10%, less than 5%; or5%-15%; and DP4+=greater than 15%, greater than 20%, greater than 30%,greater than 40%, greater than 50%; or 15%-75%, 20%-40% or 25%-35%.

In some embodiments, the oligosaccharide degree of polymerization (DP)distribution for the one or more oligosaccharides after combining theone or more sugars with the catalyst (e.g., at 2, 3, 4, 8, 12, 24, or 48hours after combining the one or more sugars with the catalyst) is anyone of entries (1)-(192) of Table 1A.

TABLE 1A Entry DP4+ (%) DP3 (%) DP2 (%) 1 20-25 0-5 0-5 2 20-25 0-5 5-10 3 20-25 0-5 10-15 4 20-25 0-5 15-20 5 20-25 0-5 20-25 6 20-25 0-525-30 7 20-25  5-10 0-5 8 20-25  5-10  5-10 9 20-25  5-10 10-15 10 20-25 5-10 15-20 11 20-25  5-10 20-25 12 20-25  5-10 25-30 13 20-25 10-15 0-514 20-25 10-15  5-10 15 20-25 10-15 10-15 16 20-25 10-15 15-20 17 20-2510-15 20-25 18 20-25 10-15 25-30 19 20-25 15-20 0-5 20 20-25 15-20  5-1021 20-25 15-20 10-15 22 20-25 15-20 15-20 23 20-25 15-20 20-25 24 20-2515-20 25-30 25 20-25 20-25 0-5 26 20-25 20-25  5-10 27 20-25 20-25 10-1528 20-25 20-25 15-20 29 20-25 20-25 20-25 30 20-25 20-25 25-30 31 25-300-5 0-5 32 25-30 0-5  5-10 33 25-30 0-5 10-15 34 25-30 0-5 15-20 3525-30 0-5 20-25 36 25-30 0-5 25-30 37 25-30  5-10 0-5 38 25-30  5-10 5-10 39 25-30  5-10 10-15 40 25-30  5-10 15-20 41 25-30  5-10 20-25 4225-30  5-10 25-30 43 25-30 10-15 0-5 44 25-30 10-15  5-10 45 25-30 10-1510-15 46 25-30 10-15 15-20 47 25-30 10-15 20-25 48 25-30 10-15 25-30 4925-30 15-20 0-5 50 25-30 15-20  5-10 51 25-30 15-20 10-15 52 25-30 15-2015-20 53 25-30 15-20 20-25 54 25-30 15-20 25-30 55 25-30 20-25 0-5 5625-30 20-25  5-10 57 25-30 20-25 10-15 58 25-30 20-25 15-20 59 25-3020-25 20-25 60 25-30 20-25 25-30 61 30-35 0-5 0-5 62 30-35 0-5  5-10 6330-35 0-5 10-15 64 30-35 0-5 15-20 65 30-35 0-5 20-25 66 30-35 0-5 25-3067 30-35  5-10 0-5 68 30-35  5-10  5-10 69 30-35  5-10 10-15 70 30-35 5-10 15-20 71 30-35  5-10 20-25 72 30-35  5-10 25-30 73 30-35 10-15 0-574 30-35 10-15  5-10 75 30-35 10-15 10-15 76 30-35 10-15 15-20 77 30-3510-15 20-25 78 30-35 10-15 25-30 79 30-35 15-20 0-5 80 30-35 15-20  5-1081 30-35 15-20 10-15 82 30-35 15-20 15-20 83 30-35 15-20 20-25 84 30-3515-20 25-30 85 30-35 20-25 0-5 86 30-35 20-25  5-10 87 30-35 20-25 10-1588 30-35 20-25 15-20 89 30-35 20-25 20-25 90 30-35 20-25 25-30 91 35-400-5 0-5 92 35-40 0-5  5-10 93 35-40 0-5 10-15 94 35-40 0-5 15-20 9535-40 0-5 20-25 96 35-40 0-5 25-30 97 35-40  5-10 0-5 98 35-40  5-10 5-10 99 35-40  5-10 10-15 100 35-40  5-10 15-20 101 35-40  5-10 20-25102 35-40  5-10 25-30 103 35-40 10-15 0-5 104 35-40 10-15  5-10 10535-40 10-15 10-15 106 35-40 10-15 15-20 107 35-40 10-15 20-25 108 35-4010-15 25-30 109 35-40 15-20 0-5 110 35-40 15-20  5-10 111 35-40 15-2010-15 112 35-40 15-20 15-20 113 35-40 15-20 20-25 114 35-40 15-20 25-30115 35-40 20-25 0-5 116 35-40 20-25  5-10 117 35-40 20-25 10-15 11835-40 20-25 15-20 119 35-40 20-25 20-25 120 35-40 20-25 25-30 121 40-450-5 0-5 122 40-45 0-5  5-10 123 40-45 0-5 10-15 124 40-45 0-5 15-20 12540-45 0-5 20-25 126 40-45 0-5 25-30 127 40-45  5-10 0-5 128 40-45  5-10 5-10 129 40-45  5-10 10-15 130 40-45  5-10 15-20 131 40-45  5-10 20-25132 40-45  5-10 25-30 133 40-45 10-15 0-5 134 40-45 10-15  5-10 13540-45 10-15 10-15 136 40-45 10-15 15-20 137 40-45 10-15 20-25 138 40-4510-15 25-30 139 40-45 15-20 0-5 140 40-45 15-20  5-10 141 40-45 15-2010-15 142 40-45 15-20 15-20 143 40-45 15-20 20-25 144 40-45 15-20 25-30145 40-45 20-25 0-5 146 40-45 20-25  5-10 147 40-45 20-25 10-15 14840-45 20-25 15-20 149 40-45 20-25 20-25 150 40-45 20-25 25-30 151 >500-5 0-5 152 >50 0-5  5-10 153 >50 0-5 10-15 154 >50 0-5 15-20 155 >500-5 20-25 156 >50 0-5 25-30 157 >50  5-10 0-5 158 >50  5-10  5-10159 >50  5-10 10-15 160 >50  5-10 15-20 161 >50  5-10 20-25 162 >50 5-10 25-30 163 >50 10-15 0-5 164 >50 10-15  5-10 165 >50 10-15 10-15166 >50 10-15 15-20 167 >50 10-15 20-25 168 >50 10-15 25-30 169 >5015-20 0-5 170 >50 15-20  5-10 171 >50 15-20 10-15 172 >50 15-20 15-20173 >50 15-20 20-25 174 >50 15-20 25-30 175 >50 20-25 0-5 176 >50 20-25 5-10 177 >50 20-25 10-15 178 >50 20-25 15-20 179 >50 20-25 20-25180 >60 10-20 10-20 181 >60  5-10 10-20 182 >60  0-10  0-10 183 >7010-20 10-20 184 >70  5-10 10-20 185 >70  0-10  0-10 186 >80 10-20 10-20187 >80  5-10 10-20 188 >80  0-10  0-10 189 >85 10-20 10-20 190 >85 0-10  0-10 191 >85  0-10 0-5 192 >90  0-10  0-10

The yield of conversion for the one or more sugars to the one or moreoligosaccharides in the methods described herein can be determined byany suitable method known in the art, including, for example, highperformance liquid chromatography (HPLC). In some embodiments, the yieldof conversion to one or more oligosaccharides to with DP>1 aftercombining the one or more sugars with the catalyst (e.g., at 2, 3, 4, 8,12, 24, or 48 hours after combining the one or more sugars with thecatalyst) is greater than about 50% (or greater than about 55%, 60%,65%, 70%, 75%, 80%, 85%, 90%, 95%, or 98%). In some embodiments, theyield of conversion to one or more oligosaccharides of >DP2 aftercombining the one or more sugars with the catalyst (e.g., at 2, 3, 4, 8,12, 24, or 48 hours after combining the one or more sugars with thecatalyst) is greater than 30% (or greater than 35%, 40%, 45%, 50%, 55%.60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 98%).

In some embodiments, the methods described herein produce anoligosaccharide composition having lower levels of degradation products,resulting in relatively higher selectivity. The molar yield to sugardegradation products and selectivity may be determined by any suitablemethod known in the art, including, for example, HPLC. In someembodiments, the amount of sugar degradation products after combiningthe one or more sugars with the catalyst (e.g., at 2, 3, 4, 8, 12, 24,or 48 hours after combining the one or more sugars with the catalyst) isless than about 10% (or less than about 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%,1%, 0.75%, 0.5%, 0.25%, or 0.1%), such as less than about 10% of any oneor combination of 1,6-anhydroglucose (levoglucosan),5-hydroxymethylfurfural, 2-furaldehyde, acetic acid, formic acid,levulinic acid and/or humins. In some embodiments, the molar selectivityto oligosaccharide product after combining the one or more sugars withthe catalyst (e.g., at 2, 3, 4, 8, 12, 24, or 48 hours after combiningthe one or more sugars with the catalyst) is greater than about 90% (orgreater than about 95%, 97%, 98%, 99%, 99.5%, or 99.9%).

In some variations, at least 10 dry wt % of the oligosaccharidecomposition produced according to the methods described herein has adegree of polymerization of at least 3. In some embodiments, at least 10dry wt %, at least 20 dry wt %, at least 30 dry wt %, at least 40 dry wt%, at least 50 dry wt %, at least 60 dry wt %, at least 70 wt %, between10 to 90 dry wt %, between 20 to 80 dry wt %, between 30 to 80 dry wt %,between 50 to 80 dry wt %, or between 70 to 80 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3.

In some variations, the oligosaccharide composition produced accordingto methods described herein has a DP3+ of at least 10% on a dry-weightbasis. In certain variations, the oligosaccharide composition producedaccording to methods described herein has a DP3+ of at least 10% on adry-weight basis, at least 20% on a dry-weight basis, at least 30% on adry-weight basis, at least 40% on a dry-weight basis, at least 50% on adry-weight basis, at least 60% on a dry-weight basis, at least 70% on adry-weight basis, between 10 to 90% on a dry-weight basis, between 20 to80% on a dry-weight basis, between 30 to 80% on a dry-weight basis,between 50 to 80% on a dry-weight basis, or between 70 to 80% on adry-weight basis.

In some variations, the oligosaccharide composition has an averagemolecular weight of between 100 g/mol and 2000 g/mol, or between 300g/mol and 1800 g/mol, or between 300 g/mol and 1700 g/mol, or between500 g/mol and 1500 g/mol; or about 300 g/mol, 350 g/mol, 400 g/mol, 450g/mol, 500 g/mol, 550 g/mol, 600 g/mol, 650 g/mol, 700 g/mol, 750 g/mol,800 g/mol, 850 g/mol, 900 g/mol, 950 g/mol, 1000 g/mol, 1100 g/mol, 1200g/mol, 1300 g/mol, 1400 g/mol, 1500 g/mol, 1600 g/mol, 1700 g/mol, orabout 1800 g/mol. In certain variations of the foregoing, the averagemolecular weight of the oligosaccharide composition is determined as thenumber average molecular weight. In other variations, the averagemolecular weight of the oligosaccharide composition is determined as theweight average molecular weight. In yet another variation, theoligosaccharide composition contains only monosaccharide units that havethe same molecular weight, in which case the number average molecularweight is identical to the product of the average degree ofpolymerization and the molecular weight of the monosaccharide unit.

Glass Transition Temperature

In some variations, “glass transition” refers to the reversibletransition of some compounds from a hard and relatively brittle state toa softer, flexible state. In some variations, “glass transitiontemperature” refers to the temperature determined by differentialscanning calorimetry.

The glass transition temperature of a material can impart desirablecharacteristics to that material, and/or can impart desirablecharacteristics to a composition comprising that material. For example,varying the glass transition temperature of the oligosaccharidecomposition can affect its blendability in the animal feed composition.In some embodiments, the methods described herein are used to produceone or more oligosaccharides with a specific glass transitiontemperature, or within a glass transition temperature range. In somevariations, the glass transition temperature of one or moreoligosaccharides produced according to the methods described hereinimparts desirable characteristics to the one or more oligosaccharides(e.g., texture, storage, or processing characteristics). In certainvariations, the glass transition temperature of the one or moreoligosaccharides imparts desirable characteristics to a compositionincluding the one or more oligosaccharides (e.g., texture, storage, orprocessing characteristics).

For example, in some variations, animal feed compositions or animal feedpre-mix that include the one or more oligosaccharides with a lower glasstransition temperature have a softer texture than animal feedcompositions or animal feed pre-mix that includes the one or moreoligosaccharides with a higher glass transition temperature, or animalfeed compositions or animal feed pre-mix that do not include the one ormore oligosaccharides. In other variations, animal feed compositionsincluding the one or more oligosaccharides with a higher glasstransition temperature have reduced caking and can be dried at highertemperatures than animal feed compositions or animal feed pre-mixincluding the one or more oligosaccharides with a lower glass transitiontemperature, or animal feed compositions or animal feed pre-mix that donot include the one or more oligosaccharides.

In some embodiments, the glass transition temperature of the one or moreoligosaccharides when prepared in a dry powder form with a moisturecontent below 6% is at least −20 degrees Celsius (° C.), at least −10degrees Celsius, at least 0 degrees Celsius, at least 10 degreesCelsius, at least 20 degrees Celsius, at least 30 degrees Celsius, atleast 40 degrees Celsius, at least 50 degrees Celsius, at least 60degrees Celsius, at least 70 degrees Celsius, at least 80 degreesCelsius, at least 90 degrees Celsius, or at least 100 degrees Celsius.In certain embodiments, the glass transition temperature of the one ormore oligosaccharides is between 40 degrees Celsius and 80 degreesCelsius.

In some variations, the oligosaccharide composition has a glasstransition temperature of at least −20 degrees Celsius (° C.), at least−10 degrees Celsius, at least 0 degrees Celsius, at least 10 degreesCelsius, at least 20 degrees Celsius, at least 30 degrees Celsius, atleast 40 degrees Celsius, at least 50 degrees Celsius, at least 60degrees Celsius, at least 70 degrees Celsius, at least 80 degreesCelsius, at least 90 degrees Celsius, or at least 100 degrees Celsius,when measured at less than 10 wt % water. In certain embodiments, theoligosaccharide composition has a glass transition temperature ofbetween 40 degrees Celsius and 80 degrees Celsius, when measured at lessthan 10 wt % water. In one variation, the oligosaccharide compositionhas a glass transition temperature between −20 and 115 degrees Celsius,when measured at less than 10 wt % water.

Hygroscopicity

In some variations, “hygroscopicity” refers to the ability of a compoundto attract and hold water molecules from the surrounding environment.The hygroscopicity of a material can impart desirable characteristics tothat material, and/or can impart desirable characteristics to acomposition comprising that material. In some embodiments, the methodsdescribed herein are used to produce one or more oligosaccharides with aspecific hygroscopicity value or a range of hygroscopicity values. Insome variations, the hygroscopicity of one or more oligosaccharidesproduced according to the methods described herein imparts desirablecharacteristics to the one or more oligosaccharides (e.g., texture,storage, or processing characteristics). In certain variations, thehygroscopicity of the one or more oligosaccharides imparts desirablecharacteristics to a composition including the one or moreoligosaccharides (e.g., texture, storage, or processingcharacteristics).

For example, in some variations, animal feed compositions or animal feedpre-mix that include the one or more oligosaccharides with a higherhygroscopicity have a softer texture than animal feed compositions oranimal feed pre-mix that include the one or more oligosaccharides with alower hygroscopicity, or animal feed compositions or animal feed pre-mixwithout the one or more oligosaccharides. In certain variations, the oneor more oligosaccharides with a higher hygroscopicity are included inanimal feed compositions or animal feed pre-mix to reduce wateractivity, increase shelf life, produce a softer composition, produce amoister composition, and/or enhance the surface sheen of thecomposition.

In other variations, animal feed compositions including the one or moreoligosaccharides with a lower hygroscopicity have reduced caking and canbe dried at a higher temperature than animal feed compositions includingthe one or more oligosaccharides with a higher hygroscopicity, or animalfeed compositions without the one or more oligosaccharides. In certainvariations, the one or more oligosaccharides with a lower hygroscopicityare included in animal feed compositions to increase crispness, increaseshelf life, reduce clumping, reduce caking, improve, and/or enhance theappearance of the composition.

The hygroscopicity of a composition, including the one or moreoligosaccharides, can be determined by measuring the mass gain of thecomposition after equilibration in a fixed water activity atmosphere(e.g., a desiccator held at a fixed relative humidity).

In some embodiments, the hygroscopicity of the one or moreoligosaccharides is at least 5% moisture content at a water activity ofat least 0.6, at least 10% moisture content at a water activity of atleast 0.6, at least 15% moisture content at a water activity of at least0.6, at least 20% moisture content at a water activity of at least 0.6,or at least 30% moisture content at a water activity of at least 0.6. Incertain embodiments, the hygroscopicity of the one or moreoligosaccharides is between 5% moisture content and 15% moisture contentat a water activity of at least 0.6.

In certain variations, the oligosaccharide composition has ahygroscopicity of at least 5%, at least 10%, at least 15%, at least 20%,or at least 30% moisture content, when measured at a water activity ofat least 0.6. In certain embodiments, the oligosaccharide compositionhas a hygroscopicity of between 5% moisture content and 15% moisturecontent, when measured at a water activity of at least 0.6.

In one variation, the oligosaccharide composition has a hygroscopicityof at least 0.05 g/g, when measured at a water activity of 0.6.

In some embodiments, the mean degree of polymerization (DP), glasstransition temperature (Tg), and hygroscopicity of the oligosaccharidecomposition produced by combining the one or more sugars with thecatalyst (e.g., at 2, 3, 4, 8, 12, 24, or 48 hours after combining theone or more sugars with the catalyst) is any one of entries (1)-(180) ofTable 1B.

TABLE 1B Tg at <10 Hygroscopicity Mean wt % H2O (wt % H2O @ Number DP (°C.) 0.6 Aw) 1  5-10 >50  >5% 2  5-10 >50  >5% 3  5-10 >50  >5% 4 5-10 >50  >5% 5  5-10 >50  >5% 6  5-10 >50 >10% 7  5-10 >50 >10% 8 5-10 >50 >10% 9  5-10 >50 >10% 10  5-10 >50 >10% 11  5-10 >50 >15% 12 5-10 >50 >15% 13  5-10 >50 >15% 14  5-10 >50 >15% 15  5-10 >50 >15% 16 5-10 >50  >5% 17  5-10 >50  >5% 18  5-10 >50  >5% 19  5-10 >50  >5% 20 5-10 >50  >5% 21  5-10 >50 >10% 22  5-10 >50 >10% 23  5-10 >50 >10% 24 5-10 >50 >10% 25  5-10 >50 >10% 26  5-10 >50 >15% 27  5-10 >50 >15% 28 5-10 >50 >15% 29  5-10 >50 >15% 30  5-10 >50 >15% 31  5-10 >75  >5% 32 5-10 >75  >5% 33  5-10 >75  >5% 34  5-10 >75  >5% 35  5-10 >75  >5% 36 5-10 >75 >10% 37  5-10 >75 >10% 38  5-10 >75 >10% 39  5-10 >75 >10% 40 5-10 >75 >10% 41  5-10 >75 >15% 42  5-10 >75 >15% 43  5-10 >75 >15% 44 5-10 >75 >15% 45  5-10 >75 >15% 46  5-10 >75  >5% 47  5-10 >75  >5% 48 5-10 >75  >5% 49  5-10 >75  >5% 50  5-10 >75  >5% 51  5-10 >75 >10% 52 5-10 >75 >10% 53  5-10 >75 >10% 54  5-10 >75 >10% 55  5-10 >75 >10% 56 5-10 >75 >15% 57  5-10 >75 >15% 58  5-10 >75 >15% 59  5-10 >75 >15% 60 5-10 >75 >15% 61  5-10 >100  >5% 62  5-10 >100  >5% 63  5-10 >100  >5%64  5-10 >100  >5% 65  5-10 >100  >5% 66  5-10 >100 >10% 67 5-10 >100 >10% 68  5-10 >100 >10% 69  5-10 >100 >10% 70  5-10 >100 >10%71  5-10 >100 >15% 72  5-10 >100 >15% 73  5-10 >100 >15% 74 5-10 >100 >15% 75  5-10 >100 >15% 76  5-10 >100  >5% 77  5-10 >100  >5%78  5-10 >100  >5% 79  5-10 >100  >5% 80  5-10 >100  >5% 81 5-10 >100 >10% 82  5-10 >100 >10% 83  5-10 >100 >10% 84  5-10 >100 >10%85  5-10 >100 >10% 86  5-10 >100 >15% 87  5-10 >100 >15% 88 5-10 >100 >15% 89  5-10 >100 >15% 90  5-10 >100 >15% 91 10-15 >50  >5%92 10-15 >50  >5% 93 10-15 >50  >5% 94 10-15 >50  >5% 95 10-15 >50  >5%96 10-15 >50 >10% 97 10-15 >50 >10% 98 10-15 >50 >10% 99 10-15 >50 >10%100 10-15 >50 >10% 101 10-15 >50 >15% 102 10-15 >50 >15% 10310-15 >50 >15% 104 10-15 >50 >15% 105 10-15 >50 >15% 106 10-15 >50  >5%107 10-15 >50  >5% 108 10-15 >50  >5% 109 10-15 >50  >5% 110 10-15 >50 >5% 111 10-15 >50 >10% 112 10-15 >50 >10% 113 10-15 >50 >10% 11410-15 >50 >10% 115 10-15 >50 >10% 116 10-15 >50 >15% 117 10-15 >50 >15%118 10-15 >50 >15% 119 10-15 >50 >15% 120 10-15 >50 >15% 121 10-15 >75 >5% 122 10-15 >75  >5% 123 10-15 >75  >5% 124 10-15 >75  >5% 12510-15 >75  >5% 126 10-15 >75 >10% 127 10-15 >75 >10% 128 10-15 >75 >10%129 10-15 >75 >10% 130 10-15 >75 >10% 131 10-15 >75 >15% 13210-15 >75 >15% 133 10-15 >75 >15% 134 10-15 >75 >15% 135 10-15 >75 >15%136 10-15 >75  >5% 137 10-15 >75  >5% 138 10-15 >75  >5% 139 10-15 >75 >5% 140 10-15 >75  >5% 141 10-15 >75 >10% 142 10-15 >75 >10% 14310-15 >75 >10% 144 10-15 >75 >10% 145 10-15 >75 >10% 146 10-15 >75 >15%147 10-15 >75 >15% 148 10-15 >75 >15% 149 10-15 >75 >15% 15010-15 >75 >15% 151 10-15 >100  >5% 152 10-15 >100  >5% 153 10-15 >100 >5% 154 10-15 >100  >5% 155 10-15 >100  >5% 156 10-15 >100 >10% 15710-15 >100 >10% 158 10-15 >100 >10% 159 10-15 >100 >10% 16010-15 >100 >10% 161 10-15 >100 >15% 162 10-15 >100 >15% 16310-15 >100 >15% 164 10-15 >100 >15% 165 10-15 >100 >15% 166 10-15 >100 >5% 167 10-15 >100  >5% 168 10-15 >100  >5% 169 10-15 >100  >5% 17010-15 >100  >5% 171 10-15 >100 >10% 172 10-15 >100 >10% 17310-15 >100 >10% 174 10-15 >100 >10% 175 10-15 >100 >10% 17610-15 >100 >15% 177 10-15 >100 >15% 178 10-15 >100 >15% 17910-15 >100 >15% 180 10-15 >100 >15%

Glycosidic Bond Type Distribution

In certain variations, the oligosaccharide composition producedaccording to the methods described herein has a distribution ofglycosidic bond linkages. The distribution of glycosidic bond types maybe determined by any suitable methods known in the art, including, forexample, proton NMR or two dimentional J-resolved nuclear magneticresonance spectroscopy (2D-JRES NMR). In some variations, thedistribution of glycosidic bond types described herein is determined by2D-JRES NMR.

As described above, the oligosaccharide composition may comprise hexosesugar monomers (such as glucose) or pentose sugar monomers (such asxylose), or combinations thereof. It should be understood by one ofskill in the art that certain types of glycosidic linkages may not beapplicable to oligosaccharides comprising pentose sugar monomers.

In some variations, the oligosaccharide composition has a bonddistribution with:

-   -   (i) α-(1,2) glycosidic linkages;    -   (ii) α-(1,3) glycosidic linkages;    -   (iii) α-(1,4) glycosidic linkages;    -   (iv) α-(1,6) glycosidic linkages;    -   (v) β-(1,2) glycosidic linkages;    -   (vi) β-(1,3) glycosidic linkages;    -   (vii) β-(1,4) glycosidic linkages; or    -   (viii) β-(1,6) glycosidic linkages,    -   or any combination of (i) to (viii) above.

For example, in some variations, the oligosaccharide composition has abond distribution with a combination of (ii) and (vi) glycosidiclinkages. In other variations, the oligosaccharide composition has abond distribution with a combination of (i), (viii), and (iv) glycosidiclinkages. In another variation, the oligosaccharide composition has abond distribution with a combination of (i), (ii), (v), (vi), (vii), and(viii) glycosidic linkages.

In certain variations, the oligosaccharide composition has a bonddistribution with any combination of (i), (ii), (iii), (v), (vi), and(vii) glycosidic linkages, and comprises oligosaccharides with pentosesugar monomers. In other variations, the oligosaccharide composition hasa bond distribution with any combination of (i), (ii), (iii), (iv), (v),(vi), (vii) and (viii) glycosidic linkages, and comprisesoligosaccharides with hexose sugar monomers. In still other variations,the oligosaccharide composition has a bond distribution with anycombination of (i), (ii), (iii), (iv), (v), (vi), (vii) and (viii)glycosidic linkages, and comprises oligosaccharides with hexose sugarmonomers, and oligosaccharides with pentose sugar monomers. In stillother variations, the oligosaccharide composition has a bonddistribution with any combination of (i), (ii), (iii), (iv), (v), (vi),(vii) and (viii) glycosidic linkages, and comprises oligosaccharideswith hexose sugar monomers and pentose sugar monomers. In yet anothervariation, the oligosaccharide composition has a bond distribution withany combination of (i), (ii), (iii), (iv), (v), (vi), (vii) and (viii)glycosidic linkages, and comprises oligosaccharides with hexose sugarmonomers, oligosaccharides with pentose sugar monomers, andoligosaccharides with hexose and pentose sugar monomers.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 20 mol % α-(1,2) glycosidiclinkages, less than 10 mol % α-(1,2) glycosidic linkages, less than 5mol % α-(1,2) glycosidic linkages, between 0 to 25 mol % α-(1,2)glycosidic linkages, between 1 to 25 mol % α-(1,2) glycosidic linkages,between 0 to 20 mol % α-(1,2) glycosidic linkages, between 1 to 15 mol %α-(1,2) glycosidic linkages, between 0 to 10 mol % α-(1,2) glycosidiclinkages, or between 1 to 10 mol % α-(1,2) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 50 mol % β-(1,2) glycosidiclinkages, less than 40 mol % β-(1,2) glycosidic linkages, less than 35mol % β-(1,2) glycosidic linkages, less than 30 mol % β-(1,2) glycosidiclinkages, less than 25 mol % β-(1,2) glycosidic linkages, less than 10mol % β-(1,2) glycosidic linkages, at least 1 mol % β-(1,2) glycosidiclinkages, at least 5 mol % β-(1,2) glycosidic linkages, at least 10 mol% β-(1,2) glycosidic linkages, at least 15 mol % β-(1,2) glycosidiclinkages, at least 20 mol % β-(1,2) glycosidic linkages, between 0 to 30mol % β-(1,2) glycosidic linkages, between 1 to 30 mol % β-(1,2)glycosidic linkages, between 0 to 25 mol % β-(1,2) glycosidic linkages,between 1 to 25 mol % β-(1,2) glycosidic linkages, between 10 to 30 mol% β-(1,2) glycosidic linkages, between 15 to 25 mol % β-(1,2) glycosidiclinkages, between 0 to 10 mol % β-(1,2) glycosidic linkages, between 1to 10 mol % β-(1,2) glycosidic linkages, between 10 to 50 mol % β-(1,2)glycosidic linkages, between 10 to 40 mol % β-(1,2) glycosidic linkages,between 20 to 35 mol % β-(1,2) glycosidic linkages, between 20 to 35 mol% β-(1,2) glycosidic linkages, between 20 to 50 mol % β-(1,2) glycosidiclinkages, between 30 to 40 mol % β-(1,2) glycosidic linkages, between 10to 30 mol % β-(1,2) glycosidic linkages, or between 10 to 20 mol %β-(1,2) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 40 mol % α-(1,3) glycosidiclinkages, less than 30 mol % α-(1,3) glycosidic linkages, less than 25mol % α-(1,3) glycosidic linkages, less than 20 mol % α-(1,3) glycosidiclinkages, less than 15 mol % α-(1,3) glycosidic linkages, at least 1 mol% α-(1,3) glycosidic linkages, at least 5 mol % α-(1,3) glycosidiclinkages, at least 10 mol % α-(1,3) glycosidic linkages, at least 15 mol% α-(1,3) glycosidic linkages, at least 20 mol % α-(1,3) glycosidiclinkages, at least 25 mol % α-(1,3) glycosidic linkages, between 0 to 30mol % α-(1,3) glycosidic linkages, between 1 to 30 mol % β-(1,3)glycosidic linkages, between 5 to 30 mol % (1,3) glycosidic linkages,between 10 to 25 mol % α-(1,3) glycosidic linkages, between 1 to 20 mol% α-(1,3) glycosidic linkages, or between 5 to 15 mol % α-(1,3)glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 25 mol % β-(1,3) glycosidiclinkages, less than 20 mol % β-(1,3) glycosidic linkages, less than 15mol % β-(1,3) glycosidic linkages, less than 10 mol % β-(1,3) glycosidiclinkages, at least 1 mol % β-(1,3) glycosidic linkages, at least 2 mol %β-(1,3) glycosidic linkages, at least 5 mol % β-(1,3) glycosidiclinkages, at least 10 mol % β-(1,3) glycosidic linkages, at least 15 mol% β-(1,3) glycosidic linkages, between 1 to 20 mol % β-(1,3) glycosidiclinkages, between 5 to 15 mol % β-(1,3) glycosidic linkages, between 1to 15 mol % β-(1,3) glycosidic linkages, or between 2 to 10 mol %β-(1,3) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 20 mol % α-(1,4) glycosidiclinkages, less than 15 mol % α-(1,4) glycosidic linkages, less than 10mol % α-(1,4) glycosidic linkages, less than 9 mol % α-(1,4) glycosidiclinkages, between 1 to 20 mol % α-(1,4) glycosidic linkages, between 1to 15 mol % α-(1,4) glycosidic linkages, between 2 to 15 mol % α-(1,4)glycosidic linkages, between 5 to 15 mol % α-(1,4) glycosidic linkages,between 1 to 15 mol % α-(1,4) glycosidic linkages, or between 1 to 10mol % α-(1,4) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 55 mol % β-(1,4) glycosidiclinkages, less than 50 mol % β-(1,4) glycosidic linkages, less than 45mol % β-(1,4) glycosidic linkages, less than 40 mol % β-(1,4) glycosidiclinkages, less than 35 mol % β-(1,4) glycosidic linkages, less than 25mol % β-(1,4) glycosidic linkages, less than 15 mol % β-(1,4) glycosidiclinkages, less than 10 mol % β-(1,4) glycosidic linkages, at least 1 mol% β-(1,4) glycosidic linkages, at least 5 mol % β-(1,4) glycosidiclinkages, at least 10 mol % β-(1,4) glycosidic linkages, at least 20 mol% β-(1,4) glycosidic linkages, at least 30 mol % β-(1,4) glycosidiclinkages, between 0 to 55 mol % β-(1,4) glycosidic linkages, between 5to 55 mol % β-(1,4) glycosidic linkages, between 10 to 50 mol % β-(1,4)glycosidic linkages, between 0 to 40 mol % β-(1,4) glycosidic linkages,between 1 to 40 mol % β-(1,4) glycosidic linkages, between 0 to 35 mol %β-(1,4) glycosidic linkages, between 1 to 35 mol % β-(1,4) glycosidiclinkages, between 1 to 30 mol % β-(1,4) glycosidic linkages, between 5to 25 mol % β-(1,4) glycosidic linkages, between 10 to 25 mol % β-(1,4)glycosidic linkages, between 15 to 25 mol % β-(1,4) glycosidic linkages,between 0 to 15 mol % β-(1,4) glycosidic linkages, between 1 to 15 mol %β-(1,4) glycosidic linkages, between 0 to 10 mol % β-(1,4) glycosidiclinkages, or between 1 to 10 mol % β-(1,4) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 30 mol % α-(1,6) glycosidiclinkages, less than 25 mol % α-(1,6) glycosidic linkages, less than 20mol % α-(1,6) glycosidic linkages, less than 19 mol % α-(1,6) glycosidiclinkages, less than 15 mol % α-(1,6) glycosidic linkages, less than 10mol % α-(1,6) glycosidic linkages, between 0 to 30 mol % α-(1,6)glycosidic linkages, between 1 to 30 mol % α-(1,6) glycosidic linkages,between 5 to 25 mol % α-(1,6) glycosidic linkages, between 0 to 25 mol %α-(1,6) glycosidic linkages, between 1 to 25 mol % α-(1,6) glycosidiclinkages, between 0 to 20 mol % α-(1,6) glycosidic linkages, between 0to 15 mol % α-(1,6) glycosidic linkages, between 1 to 15 mol % α-(1,6)glycosidic linkages, between 0 to 10 mol % α-(1,6) glycosidic linkages,or between 1 to 10 mol % α-(1,6) glycosidic linkages. In someembodiments, the oligosaccharide composition comprises oligosaccharideswith hexose sugar monomers.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 55 mol % β-(1,6) glycosidiclinkages, less than 50 mol % β-(1,6) glycosidic linkages, less than 35mol % β-(1,6) glycosidic linkages, less than 30 mol % β-(1,6) glycosidiclinkages, at least 1 mol % β-(1,6) glycosidic linkages, at least 5 mol %β-(1,6) glycosidic linkages, at least 10 mol % β-(1,6) glycosidiclinkages, at least 15 mol % β-(1,6) glycosidic linkages, at least 20 mol% β-(1,6) glycosidic linkages, at least 25 mol % β-(1,6) glycosidiclinkages, at least 20 mol % β-(1,6) glycosidic linkages, at least 25 mol% β-(1,6) glycosidic linkages, at least 30 mol % β-(1,6) glycosidiclinkages, between 10 to 55 mol % β-(1,6) glycosidic linkages, between 5to 55 mol % β-(1,6) glycosidic linkages, between 15 to 55 mol % β-(1,6)glycosidic linkages, between 20 to 55 mol % β-(1,6) glycosidic linkages,between 20 to 50 mol % β-(1,6) glycosidic linkages, between 25 to 55 mol% β-(1,6) glycosidic linkages, between 25 to 50 mol % β-(1,6) glycosidiclinkages, between 5 to 40 mol % β-(1,6) glycosidic linkages, between 5to 30 mol % β-(1,6) glycosidic linkages, between 10 to 35 mol % β-(1,6)glycosidic linkages, between 5 to 20 mol % β-(1,6) glycosidic linkages,between 5 to 15 mol % β-(1,6) glycosidic linkages, between 8 to 15 mol %β-(1,6) glycosidic linkages, or between 15 to 30 mol % β-(1,6)glycosidic linkages. In some embodiments, the oligosaccharidecomposition comprises oligosaccharides with hexose sugar monomers.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 1 mol % α-(1,3) glycosidic linkages.In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 10 mol % α-(1,3) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 1 mol % β-(1,3) glycosidic linkages.In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 10 mol % β-(1,3) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 15 mol % β-(1,6) glycosidic linkages.In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 10 mol % β-(1,6) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 15 mol % β-(1,2) glycosidic linkages.In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 10 mol % β-(1,2) glycosidic linkages.

It should be understood that the glycosidic linkage distributionsdescribed herein for the various types of linkages (e.g., α-(1,2),α-(1,3), α-(1,4), α-(1,6), β-(1,2), β-(1,3), β-(1,4), or β-(1,6)glycosidic linkages) may be combined as if each and every combinationwere individually listed, as applicable.

In some variations, the distribution of glycosidic bond types describedabove for any of the oligosaccharide compositions herein is determinedby two dimensional J-resolved nuclear magnetic resonance (2D-JRES NMR)spectroscopy.

In certain variations, the oligosaccharide composition comprises onlyhexose sugar monomers, and has any glycosidic bond type distribution asdescribed herein. In some variations, the oligosaccharide compositioncomprises only pentose sugar monomers, and has any glycosidic bond typedistribution as described herein, as applicable. In yet othervariations, the oligosaccharide composition comprises both pentose andhexose sugar monomers, and has any glycosidic bond type distribution asdescribed herein, as applicable.

It should be further understood that variations for the type ofoligosaccharides present in the composition, as well as the degree ofpolymerization, glass transition temperature, and hygroscopicity of theoligosaccharide composition, may be combined as if each and everycombination were listed separately. For example, in some variations, theoligosaccharide composition is made up of a plurality ofoligosaccharides, wherein the composition has a glycosidic bonddistribution of:

-   -   at least 1 mol % α-(1,3) glycosidic linkages;    -   at least 1 mol % β-(1,3) glycosidic linkages;    -   at least 15 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages, and    -   wherein at least 10 dry wt % of the oligosaccharide composition        has a degree of polymerization of at least 3. In some        variations, at least 50 dry wt %, or between 65 and 80 dry wt %        of the oligosaccharide composition has a degree of        polymerization of at least 3.

For example, in some variations, the oligosaccharide composition has aglycosidic bond type distribution of less than 20 mol % α-(1,4)glycosidic linkages, and less than 30 mol % α-(1,6) glycosidic linkages.In some variations, at least 10 dry wt % of the oligosaccharidecomposition has a degree of polymerization of at least 3. In somevariations, at least 50 dry wt %, or between 65 and 80 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3.

In another variation, the oligosaccharide composition comprises aglycosidic bond type distribution of between 0 to 15 mol % α-(1,2)glycosidic linkages; between 0 to 30 mol % β-(1,2) glycosidic linkages;between 1 to 30 mol % α-(1,3) glycosidic linkages; between 1 to 20 mol %β-(1,3) glycosidic linkages; between 0 to 55 mol % β-(1,4) glycosidiclinkages; and between 15 to 55 mol % β-(1,6) glycosidic linkages. Insome variations, at least 10 dry wt % of the oligosaccharide compositionhas a degree of polymerization of at least 3. In some variations, atleast 50 dry wt %, or between 65 and 80 dry wt % of the oligosaccharidecomposition has a degree of polymerization of at least 3.

In yet another variation, the oligosaccharide composition has aglycosidic bond type distribution of between 0 to 15 mol % α-(1,2)glycosidic linkages; between 10 to 30 mol % β-(1,2) glycosidic linkages;between 5 to 30 mol % α-(1,3) glycosidic linkages; between 1 to 20 mol %β-(1,3) glycosidic linkages; between 0 to 15 mol % β-(1,4) glycosidiclinkages; between 20 to 55 mol % β-(1,6) glycosidic linkages; less than20 mol % α-(1,4) glycosidic linkages; and less than 15 mol % α-(1,6)glycosidic linkages. In some variations, at least 10 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3. In some variations, at least 50 dry wt %, or between 65 and 80 dry wt% of the oligosaccharide composition has a degree of polymerization ofat least 3.

In still other variations, the oligosaccharide composition has aglycosidic bond type distribution of between 0 to 10 mol % α-(1,2)glycosidic linkages, between 15 to 25 mol % β-(1,2) glycosidic linkages,between 10 to 25 mol % α-(1,3) glycosidic linkages, between 5 to 15 mol% β-(1,3) glycosidic linkages, between 5 to 15 mol % α-(1,4) glycosidiclinkages, between 0 to 10 mol % β-(1,4) glycosidic linkages, between 0to 10 mol % α-(1,6) glycosidic linkages, and between 25 to 50 mol %β-(1,6) glycosidic linkages. In some variations, at least 10 dry wt % ofthe oligosaccharide composition has a degree of polymerization of atleast 3. In some variations, at least 50 dry wt %, or between 65 and 80dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In certain variations, the oligosaccharide composition has a glycosidicbond type distribution of between 0 to 15 mol % α-(1,2) glycosidiclinkages; between 0 to 15 mol % β-(1,2) glycosidic linkages; between 1to 20 mol % α-(1,3) glycosidic linkages; between 1 to 15 mol % β-(1,3)glycosidic linkages; between 5 to 55 mol % β-(1,4) glycosidic linkages;between 15 to 55 mol % β-(1,6) glycosidic linkages; less than 20 mol %α-(1,4) glycosidic linkages; and less than 30 mol % α-(1,6) glycosidiclinkages. In some variations, at least 10 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3. In some variations, at least 50 dry wt %, or between 65 and 80 dry wt% of the oligosaccharide composition has a degree of polymerization ofat least 3.

In yet other variations, the oligosaccharide composition has aglycosidic bond type distribution of between 0 to 10 mol % α-(1,2)glycosidic linkages, between 0 to 10 mol % β-(1,2) glycosidic linkages,between 5 to 15 mol % α-(1,3) glycosidic linkages, between 2 to 10 mol %β-(1,3) glycosidic linkages, between 2 to 15 mol % α-(1,4) glycosidiclinkages, between 10 to 50 mol % β-(1,4) glycosidic linkages, between 5to 25 mol % α-(1,6) glycosidic linkages, and between 20 to 50 mol %β-(1,6) glycosidic linkages. In some variations, at least 10 dry wt % ofthe oligosaccharide composition has a degree of polymerization of atleast 3. In some variations, at least 50 dry wt %, or between 65 and 80dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In other variations, the oligosaccharide composition has a glycosidicbond type distribution of between 0 to 15 mol % α-(1,2) glycosidiclinkages, between 0 to 30 mol % β-(1,2) glycosidic linkages, between 5to 30 mol % α-(1,3) glycosidic linkages, between 1 to 20 mol % β-(1,3)glycosidic linkages, between 1 to 20 mol % α-(1,4) glycosidic linkages,between 0 to 40 mol % β-(1,4) glycosidic linkages, between 0 to 25 mol %α-(1,6) glycosidic linkages, and between 10 to 35 mol % β-(1,6)glycosidic linkages. In some variations, at least 10 dry wt % of theoligosaccharide composition has a degree of polymerization of at least3. In some variations, at least 50 dry wt %, or between 65 and 80 dry wt% of the oligosaccharide composition has a degree of polymerization ofat least 3.

In still other variations, the oligosaccharide composition has aglycosidic bond type distribution of between 0 to 10 mol % α-(1,2)glycosidic linkages, between 0 to 25 mol % β-(1,2) glycosidic linkages,between 10 to 25 mol % α-(1,3) glycosidic linkages, between 5 to 15 mol% β-(1,3) glycosidic linkages, between 5 to 15 mol % α-(1,4) glycosidiclinkages, between 0 to 35 mol % β-(1,4) glycosidic linkages, between 0to 20 mol % α-(1,6) glycosidic linkages, and between 15 to 30 mol %β-(1,6) glycosidic linkages. In some variations, at least 10 dry wt % ofthe oligosaccharide composition has a degree of polymerization of atleast 3. In some variations, at least 50 dry wt %, or between 65 and 80dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In still other variations, the oligosaccharide composition has aglycosidic bond type distribution of at least 1 mol % α-(1,3) glycosidiclinkages, and at least 1 mol % β-(1,3) glycosidic linkages, wherein atleast 10 dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3. In some variations, the oligosaccharidecomposition further has a glycosidic bond type distribution of at least15 mol % β-(1,6) glycosidic linkages. In yet other variations, at least50 dry wt %, or between 65 and 80 dry wt % of the oligosaccharidecomposition has a degree of polymerization of at least 3.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 10 mol % α-(1,3) glycosidic linkages;and at least 10 mol % β-(1,3) glycosidic linkages. In some variations,the oligosaccharide composition has a glycosidic bond type distributionof less than 9 mol % α-(1,4) glycosidic linkages; and less than 19 mol %α-(1,6) glycosidic linkages. In some variations, the oligosaccharidecomposition further has a glycosidic bond type distribution of at least15 mol % β-(1,2) glycosidic linkages.

In other variations, the oligosaccharide composition has a glycosidicbond type distribution of less than 9 mol % α-(1,4) glycosidic linkages,and less than 19 mol % α-(1,6) glycosidic linkages.

In still other variations, the oligosaccharide composition has aglycosidic bond type distribution of between 0 to 20 mol % α-(1,2)glycosidic linkages; between 10 to 45 mol % β-(1,2) glycosidic linkages;between 1 to 30 mol % α-(1,3) glycosidic linkages; between 1 to 20 mol %β-(1,3) glycosidic linkages; between 0 to 55 mol % β-(1,4) glycosidiclinkages; and between 10 to 55 mol % β-(1,6) glycosidic linkages.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of between 10 to 20 mol % α-(1,2) glycosidiclinkages, between 23 to 31 mol % β-(1,2) glycosidic linkages, between 7to 9 mol % α-(1,3) glycosidic linkages, between 4 to 6 mol % β-(1,3)glycosidic linkages, between 0 to 2 mol % α-(1,4) glycosidic linkages,between 18 to 22 mol % β-(1,4) glycosidic linkages, between 9 to 13 mol% α-(1,6) glycosidic linkages, and between 14 to 16 mol % β-(1,6)glycosidic linkages

In yet other variations, the oligosaccharide composition has aglycosidic bond type distribution of between 10 to 12 mol % α-(1,2)glycosidic linkages, between 31 to 39 mol % β-(1,2) glycosidic linkages,between 5 to 7 mol % α-(1,3) glycosidic linkages, between 2 to 4 mol %β-(1,3) glycosidic linkages, between 0 to 2 mol % α-(1,4) glycosidiclinkages, between 19 to 23 mol % β-(1,4) glycosidic linkages, between 13to 17 mol % α-(1,6) glycosidic linkages, and between 7 to 9 mol %β-(1,6) glycosidic linkages.

In some embodiments, which may be combined with any of the foregoingembodiments, at least 10 dry wt % of the oligosaccharide composition hasa degree of polymerization of at least 3. In some variations, at least50 dry wt %, or between 65 and 80 dry wt % of the oligosaccharidecomposition has a degree of polymerization of at least 3.

Animal Feed Composition and Animal Feed Pre-Mix

In some embodiments, the oligosaccharide composition, the animal feedpre-mix, or the animal feed composition is provided to an animal toincrease the rate of weight gain for an animal, to decrease mortality,and/or to decrease the feed conversion ratio for an animal. In someembodiments, the oligosaccharide composition, the animal feed pre-mix,or the animal feed composition is provided to an animal population todecrease mortality and/or decrease variability of the final body weightacross the population.

In certain embodiments, feeding an animal the oligosaccharidecomposition, the animal feed pre-mix, or the animal feed composition mayhave beneficial health effects, including, for example, reducingmortality, improving gut microflora, improving nutrient absorption,maintaining gastrointestinal health, and/or reducing the need forantibiotics.

a) Inclusion Rate

A person of skill in the art would recognize that the inclusion rate maybe different for different types of animal, and may be different fordifferent breeds of one type of animal (for example, different breeds ofbroiler chickens or swine). The inclusion rate may also be differentdepending on age of the animal (for example, chickens in a grower phasecompared to a finisher phase; or swine in nursery phase compared togrower phase).

In some embodiments, the oligosaccharide composition may be provided toan animal at an inclusion rate of less than 0.01 mg/kg, 0.05 mg/kg, 0.1mg/kg, 1 mg/kg, 10 mg/kg, 50 mg/kg, 100 mg/kg, 200 mg/kg, 300 mg/kg, 400mg/kg, 500 mg/kg, 600 mg/kg, 700 mg/kg, 800 mg/kg, 900 mg/kg, 1000mg/kg, 1500 mg/kg, 2000 mg/kg, 2500 mg/kg, 3000 mg/kg, 3500 mg/kg, 4000mg/kg, 4500 mg/kg, or 5000 mg/kg. In some variations, theoligosaccharide composition may be provided to an animal at an inclusionrate of less than 5,000 ppm, less than 4,000 ppm, less than 3,000 ppm,less than 2,000 ppm, less than 2,500 ppm, less than 1,000 ppm, less than750 ppm, less than 500 ppm, less than 250 ppm, between 10 ppm to 5,000,between 10 ppm and 4,000 ppm, between 10 ppm and 3,000 ppm, between 10ppm and 2,500 ppm, between 10 ppm and 2,000 ppm, between 10 ppm and1,000 ppm, between 10 ppm and 500 ppm, between 50 pp and 500 ppm,between 1,000 ppm to 5,000 ppm, between 2,000 ppm to 5,000 ppm, between3,000 ppm to 5,000 ppm, or between 1,000 ppm to 3,000 ppm.

In some variations, inclusion rate refers to the amount ofoligosaccharide composition included in the total animal feedcomposition, on a dry weight basis. For example, adding 1 g of dryoligosaccharide composition to 999 g of dry base feed results in ananimal feed composition with an oligosaccharide composition inclusionrate of 1 g/kg, or 0.1%, or 1000 ppm.

In other variations, the inclusion rate refers to the amount of dryoligosaccharide composition included in the total animal feedcomposition, including moisture. For example, adding 1 g of dryoligosaccharide composition to 999 g of base feed including moistureresults in an animal feed composition with an oligosaccharidecomposition inclusion rate of 1 g/kg, or 0.1%, or 1000 ppm.

In yet other variations, the inclusion rate refers to the amount of dryoligosaccharide composition included in the total animal diet. Forexample, feeding an animal 1 g of dry oligosaccharide directly, whereinthe animal also otherwise consumes 999 g of feed in its diet, results inan animal diet with an oligosaccharide composition inclusion rate of 1g/kg, or 0.1%, or 1000 ppm. It should be understood that while inclusionrate may refer to the amount of dry oligosaccharide included in thetotal animal diet, the oligosaccharide composition may be provided tothe animal in any suitable form. For example, in some variations, theoligosaccharide composition may be provided to the animal as a drypowder, dry solid, mash, or syrup. In other variations, theoligosaccharide composition may be provided to the animal via drinkingwater. For example, dry oligosaccharide may be dissolved in drinkingwater to form a solution with a particular concentration, and thesolution provided to the animal.

In certain variations, the inclusion rate refers the amount of dryoligosaccharide composition included in a solution provided to theanimal (for example, as drinking water). In some variations, theconcentration of oligosaccharide composition in an aqueous solution(such as drinking water) is between 0.01 to 0.5 grams dryoligosaccharide composition per gram aqueous solution, between 0.1 to0.5 grams dry oligosaccharide composition per gram aqueous solution, orbetween 0.2 to 0.4 grams dry oligosaccharide composition per gramaqueous solution.

In some variations, the animal feed pre-mix is combined with a base feedto produce an animal feed composition. For example, in one embodiment, 2g of an animal feed pre-mix is combined with 998 g of base feed, whereinthe animal feed pre-mix comprises 50 wt % kg dry oligosaccharidecomposition per kg total premix, including moisture, resulting in ananimal feed composition with an oligosaccharide composition inclusionrate of 1 g/kg, or 0.1%, or 1000 ppm.

It should be understood that the inclusion rate of oligosaccharidecomposition may be selected based on the type of animal being fed, thegrowth stage of the animal, or the animal product produced, or anycombinations thereof. For example, the inclusion rate of oligosaccharidecomposition for a ruminant animal may be different than that selectedfor a monogastric animal. In a second example, the inclusion rate ofoligosaccharide composition selected for an animal in the grower phasemay be different than that selected for an animal in the finisher phase.In yet a third example, the inclusion rate of oligosaccharidecomposition selected for an animal producing meat may be different thanthat for an animal producing milk. In another example, the inclusionrate of oligosaccharide composition selected for an animal, such asswine, in the nursery phase may be different than that selected forswine in the grower phase.

In some embodiments, the swine feed composition further comprises copperand/or zinc. In certain variations, the swine feed composition comprisesboth copper and zinc. In certain variations, the swine feed compositioncomprises growth promoting levels of copper and/or zinc. For example, inone variation, the swine feed composition comprises (i) between 10 ppmand 500 ppm copper; and/or (ii) between 10 ppm and 5000 ppm zinc.

In some embodiments, the animal feed composition further comprises anionophore or other coccidiostat. In other embodiments, the animal feedcomposition does not comprise an ionophore. In certain variations, theanimal feed composition comprises less than 1,000 ppm, less than 500ppm, less than 100 ppm, or less than 50 ppm of an ionophore or othercoccidiostat. In some embodiments, the ionophore is monensin,salinomycin, narasin, or lasolocid, or any combinations thereof.

In some embodiments, the animal feed composition does not include anantiobiotic. In certain variations, the animal feed compositioncomprises less than 1,000 ppm, less than 500 ppm, less than 100 ppm,less than 50 ppm, less than 40 ppm, less than 30 ppm, less than 20 ppm,less than 25 ppm, less than 24 ppm, less than 23 ppm, less than 22 ppm,less than 21 ppm, less than 20 ppm, less than 19 ppm, less than 18 ppm,less than 17 ppm, less than 16 ppm, less than 15 ppm, less than 14 ppm,less than 13 ppm, less than 12 ppm, less than 11 ppm, less than 10 ppm,less than 5 ppm, or less than 1 ppm of antibiotic. In some variations,the animal feed composition comprises has than 1,000 ppm; or between 10ppm and 200 ppm, or between 50 ppm and 200 ppm, or between 500 ppm and100 ppm of antibiotic.

In some embodiments, the antibiotic is bacitracin, bacitracin methylenedisalicylate, bacitracin-zinc, virginiamycin, bambermycin, avilamycin,or efrotomycin, or any combinations thereof. In one variation, noantibiotic is fed with the oligosaccharide composition.

b) Base Feed

It should be understood by one skilled in the art that the base feedselected for an animal (such as poultry or swine), may be anutritionally sufficient diet to sustain growth. Such diets may bewell-known in the industry, and the nutritional content of such diets(including, for example, the content of apparent metabolizable energy,protein, fats, vitamins, and minerals) may fall withinindustry-recognized ranges or values.

One of skill in the art would recognize that the type of base feedcombined with the oligosaccharide composition may also vary depending onthe animal. For example, the base feed for monogastrics, such as poultryor swine, may include wheat, corn and/or soybean; and the base feed fora ruminant is typically hay or live grass.

One of skill in the art would also recognize that the type of base feedcombined with the oligosaccharide composition may also vary depending onthe growth stage of the animal, or the target animal product, or acombination thereof. For example, the base feed selected for an animalin the starter phase may be different from that in the grower phase, andthe base feed selected for an animal in the grower phase may bedifferent than that selected for an animal in the finisher phase. Inanother example, the base feed selected for an animal with a targetanimal product of meat may be different than that for an animal with atarget animal product of milk.

Suitable base feed may include, for example, additional ingredientsand/or nutrients in any suitable form (including, for example, solidform or liquid form) comprising protein, carbohydrates, and fat, used inthe body of an animal to sustain growth, repair processes, vitalprocesses, and/or furnish energy. In some variations, base feed mayinclude biomass, such as grass, grain, or legumes. In other variations,base feed may include hay, stover, straw, silage, wheat, barley, maize,sorghum, rye, oats, triticale, rice, soybeans, peas, seaweed, yeast,molasses, or any combinations thereof. In yet other variations, basefeed may include animal products, for example lactose, milk, milksolids, chicken meal, fish meal, bone meal, or blood, or anycombinations thereof. In yet other variations, base feed may includeoil, for example, plant oil or animal oil. In another variation, basefeed may include hay, straw, silage, oils, grains, legumes, bone meal,blood meal, and meat, or any combinations thereof. In still othervariations, base feed may include, for example, fodder, corn-soy baseddiets, or wheat-soy based diets.

Any other suitable compounds may be included in the animal feedcomposition, including, for example, essential amino acids, salts,minerals, protein, carbohydrates, and/or vitamins Some examples ofanimal feed compositions are provided in the Examples below.

In some variations, the base feed is a poultry feed. In someembodiments, the base feed is commercial poultry feed. In certainvariations, the base feed is a corn-soy poultry feed, while in othervariations the base feed is a wheat-soy poultry feed.

In certain variations, the poultry feed comprises an apparentmetabolizable energy of at least 1000 cal/lb, 1200 cal/lb, at least 1300cal/lb, at least 1400 cal/lb, between 1000 to 1600 cal/lb, or between1300 to 1500 cal/lb.

In some embodiments, apparent metabolizable energy is the gross energyof the feed consumed by the animal minus the gross energy contained inthe animal excreta. In other embodiments, apparent metabolizable energyis the is the gross energy of the feed consumed by the animal minus thegross energy contained in the animal excreta and gaseous products ofdigestion.

In certain variations, the poultry feed comprises a crude proteincontent of at least 5 wt %, at least 10 wt %, at least 15 wt %, at least20 wt %, at least 25 wt %, between 5 to 30 wt %, between 10 to 25 wt %,or between 15 to 25 wt %.

In some variations, the poultry feed comprises a total lysine content ofat least 0.8 wt %, at least 0.9 wt %, at least 1.0 wt %, at least 1.2 wt%, at least 1.3 wt %, between 0.8 wt % to 1.5 wt %, or between 0.9 to1.4 wt %.

In certain variations, the poultry feed comprises a total methioninecontent of at least 0.4 wt %, at least 0.5 wt %, at least 0.6 wt %, atleast 0.7 wt %, between 0.4 to 0.9 wt %, or between 0.5 to 0.8 wt %.

In certain variations, the poultry feed comprises a total sulfur aminoacid content of at least 0.6 wt %, at least 0.7 wt %, at least 0.8 wt %,at least 0.9 wt %, at least 1.0 wt %, between 0.6 to 1.2 wt %, orbetween 0.8 to 1.1 wt %.

In certain variations, the poultry feed comprises a total threoninecontent of at least 0.5 wt %, at least 0.6 wt %, at least 0.7 wt %, atleast 0.8 wt %, at least 0.9 wt %, at least 1.0 wt %, at least 1.1 wt %,between 0.6 to 1.1 wt %, or between 0.7 to 1.0 wt %.

In certain variations, the poultry feed comprises a total calciumcontent of at least 0.6 wt %, at least 0.7 wt %, at least 0.8 wt %, atleast 0.9 wt %, at least 1.0 wt %, at least 1.1 wt %, between 0.6 to 1.1wt %, between 0.7 to 1.0 wt %, or between 0.8 to 0.95 wt %.

In certain variations, the poultry feed comprises a total availablephosphorous content of at least 0.2 wt %, at least 0.3 wt %, at least0.4 wt %, at least 0.5 wt %, between 0.2 to 0.6 wt %, between 0.3 to 0.5wt %, or between 0.4 to 0.5 wt %. It should be understood that totalavailable phosphorous includes bio-available phosphorous, including, forexample, phosphorous liberated from phytic acid by phytase enzymes.Total available phosphorous may be determined, for example, fromdigestibility analysis.

In certain variations, the poultry feed comprises a total sodium contentof at least 0.05 wt %, at least 0.1 wt %, at least 0.2 wt %, at least0.25 wt %, at least 0.3 wt %, at least 0.35 wt %, between 0.05 to 0.35wt %, between 0.1 to 0.3 wt %, or between 0.2 to 0.25 wt %.

The nutritional content of the animal feed, including poultry feed andswine feed, may be determined by any suitable methods known in the art,including, for example, elemental analysis or digestibility analysis.

In certain variations, the base feed comprises copper and/or zinc. Incertain variations, the base feed comprises both copper and zinc. Incertain variations, the base feed comprises growth promoting levels ofcopper and/or zinc. For example, in one variation, the base feedcomprises (i) between 10 ppm and 500 ppm copper; and/or (ii) between 10ppm and 5000 ppm zinc.

In certain variations, the base feed includes an ionophore or othercoccidiostat. In other variations, the base feed does not include anionophore or other coccidiostat. In some variations, the base feedcomprises less than 1,000 ppm, less than 500 ppm, less than 100 ppm, orless than 50 ppm of an ionophore or other coccidiostat. In someembodiments, the ionophore is monensin, salinomycin, narasin, orlasolocid, or any combinations thereof.

In some embodiments, the base feed does not include an antiobiotic. Incertain variations, the base feed comprises less than 1,000 ppm, lessthan 500 ppm, less than 100 ppm, less than 50 ppm, less than 22 ppm, orless than 11 ppm of antibiotic. In some embodiments, the antibiotic isbacitracin, bacitracin methylene disalicylate, bacitracin-zinc,virginiamycin, bambermycin, avilamycin, or efrotomycin, or anycombinations thereof.

Starter Feed, Nursery Feed

In some variations, the base feed is a starter feed, wherein the starterfeed is provided during the first week of growth, first two weeks ofgrowth, first three weeks of growth, or first four weeks of growth. Incertain variations, the nutritional content of the starter feed isoptimized for the nutritional needs of the animal during the starterphase of growth. In some variations, the starter feed may comprisemedications and/or vaccines. The term starter feed may apply to animals,such as poultry.

In other variations, the base feed is a nursery feed, wherein thenursery feed is provided during the nursery phase. One of skill in theart would recognize that the duration of the nursery phase is determinedbased on a certain cut-off weight of the swine. In some variations, thenursury phase is the period of time until the animal reaches about 40 to60 pounds. In certain variations, the nutritional content of the nurseryfeed is optimized for the nutritional needs of the animal during thenursery phase of growth. In some variations, the nursery feed maycomprise medications and/or vaccines. The term nursery feed may apply toanimals, such as swine.

Grower Feed

In other variations, the base feed is a grower feed, wherein the growerfeed is provided during the second week of growth through the finalproductive lifetime of the animal. In some variations, the grower feedis provided from the second week of growth through the final productivelifetime of the animal, while in other variations the grower feed isprovided for a a portion of time between the second week of growththrough the final productive lifetime of the animal, or for multipleseparate periods of time between the second week of growth through thefinal productive lifetime of the animal. In some variations, the growerfeed is provided to the animal for a portion of time between the secondweek of growth until the final week of the lifetime of the animal. Forexample, such animal may be poultry.

In other variations, the base feed is a grower feed, wherein the growerfeed is provided during the grower phase. One of skill in the art wouldrecognize that the duration of the grower phase is determined based on acertain cut-off weight of the animal. In some variations, the growerphase is the period of time when the animal leaves the nursery (e.g., atabout 40 to 60 pounds as described above) until the swine reach about280 pounds. For example, such animal may be swine.

In certain variations, the nutritional content of the grower feed isoptimized to minimize cost while supporting the nutritional needs of theanimal. In some variations, the grower feed may comprise medications.

Finisher Feed

In yet other variations, the base feed is a finisher feed, wherein thefinisher feed is provided during the final period of the productivelifetime of the animal. In some variations, the final period of theproductive lifetime of the animal is the final week of the lifetime ofthe animal. In some variations, the finisher feed is provided during thefinal week, the final two weeks, the final 14 days, the final 10 days,the final 9 days, the final 8 days, the final 7 days, the final 6 days,the final 5 days, or the final 4 days of the productive lifetime of theanimal, or any portion thereof. In certain variations, the finisher feedcontains a reduced content of medication, chemicals, therapeutics, orother ingredients as compared to an earlier diet (for example, thestarter feed or finisher feed) to allow the animal to clear thosematerials from their bodies prior to consumption by humans, consumptionby other animals, or processing. For example, such animals may bepoultry.

In yet other variations, the base feed is a finisher feed, wherein thefinisher feed is provided during the finisher phase. One of skill in theart would recognize that, in some variations, the finisher phase refersto the final period of the productive lifetime of the animal duringwhich the diet of the animal is modified to purge any antibiotics thatmay not be suitable for human consumption. In some variations, duringthe finisher phase, the animal (e.g., swine) may have a weight of about270 pounds to 290 pounds. In some variations, the finisher phase may betwo or three days up to a week or two weeks. In certain variations, thefinisher feed contains a reduced content of medication, chemicals,therapeutics, or other ingredients as compared to an earlier diet (forexample, the nursery feed or grower feed) to allow the swine to clearthose materials from their bodies prior to consumption by humans,consumption by other animals, or processing. For example, such animalsmay be swine.

It should be understood that the length of time the animal is providedstarter feed, grower feed, or finisher feed may depend on the intendeduse of the animal. For example, in some embodiments the animal ispoultry, and the length of time the poultry is provided starter feed,grower feed, and finisher feed may be different if the intended use ofthe poultry is as a broiler chicken, compared to processing fortray-pack chicken meat.

It should be understood that any of the characteristics of the base feeddescribed herein, including the type of base feed, compounds included inthe base feed, or nutritional content of base feed described herein(such as apparent metabolizable energy, crude protein content, totallysine content, total methionine content, total sulfur amino acidcontent, total threonine content, total calcium content, total availablephosphorous, or total sodium content), may be combined as if each andevery combination were individually listed.

For example, in some embodiments, the base feed comprises:

-   -   (i) between 1200 to 1600 cal/lb apparent metabolizable energy;    -   (ii) between 16 to 24 wt % crude protein;    -   (iii) between 1.0 and 1.4 wt % lysine;    -   (iv) between 0.5 and 0.75 wt % methionine;    -   (v) between 0.75 and 1.1 wt % total sulfur amino acids;    -   (vi) between 0.7 and 1.0 wt % calcium;    -   (vii) between 0.35 and 0.5 wt % total available phosphorous; and    -   (viii) between 0.15 and 0.3 wt % sodium,        or any combinations of (i)-(viii) above. In some variations, the        base fee comprises at least two, at least three, at least four,        at least five, at least six, at least seven or all eight of        (i)-(viii) described above.

In certain variations, a base feed is combined with an oligosaccharidecomposition to produce an animal feed composition, wherein theoligosaccharide composition has a distribution of glycosidic bondlinkages, as described above. Thus, the animal feed composition maycomprise an oligosaccharide composition, wherein the oligosaccharidecomposition has any distribution of glycosidic bond linkages describedherein. It should be understood that the base feed may also have adistribution of glycosidic bond linkages, and that in some embodimentsthe distribution may differ from the distribution of glycosidic bondlinkages of the oligosaccharide composition.

It should be understood that the animal feed composition may comprise abase feed as described herein and an oligosaccharide compositiondescribed herein as if each and every combination were individuallylisted. For example, in some variations, provided herein is an animalfeed composition comprising (i) a base feed, and (ii) an oligosaccharidecomposition, wherein the oligosaccharide composition has a glycosidicbond type distribution of less than 20 mol % α-(1,4) glycosidiclinkages, and less than 30 mol % α-(1,6) glycosidic linkages, wherein atleast 10 dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In some variations, the oligosaccharide composition has a glycosidicbond type distribution of at least 15 mol % β-(1,6) glycosidic linkages.

In other variations, provided herein is an animal feed compositioncomprising (i) a base feed, and (ii) an oligosaccharide composition,wherein the oligosaccharide composition has a glycosidic bond typedistribution of: between 0 to 15 mol % α-(1,2) glycosidic linkages;between 0 to 30 mol % β-(1,2) glycosidic linkages; between 1 to 30 mol %α-(1,3) glycosidic linkages; between 1 to 20 mol % β-(1,3) glycosidiclinkages; between 0 to 55 mol % β-(1,4) glycosidic linkages; and between15 to 55 mol % β-(1,6) glycosidic linkages.

In certain variations, the oligosaccharide composition is present in theanimal feed composition at below 5,000 ppm, below 3,000 ppm, between 10to 1,000 ppm, or between 10 to 500 ppm weight dry oligosaccharidecomposition per weight of the animal feed composition. In still othervariations, at least 50 dry wt % of the oligosaccharide compositioncomprises one or more gluco-oligosaccharides, or at least 50 dry wt % ofthe oligosaccharide composition comprises one or moregluco-galacto-oligosaccharides. In one variation of the foregoing, theanimal feed composition is a poultry feed composition.

In some variations, the oligosaccharide composition is present in theanimal feed composition at below 5,000 ppm, below 3,000 ppm, between 10to 1,000 ppm, between 10 ppm and 750 ppm, between 10 ppm and 600 ppm,between 10 to 500 ppm, between 100 ppm and 750 ppm, between 100 ppm and600 ppm, or between 200 ppm and 600 ppm weight dry oligosaccharidecomposition per weight of the animal feed composition. In one variationof the foregoing, the animal feed composition is a swine feedcomposition.

c) Animal Feed Pre-Mix

Any suitable carrier material may be combined with the oligosaccharidecomposition to produce the animal feed pre-mix. Suitable carriermaterials may include, for example, ground rice hulls, ground oat hulls,feed grade silica gel, feed grade fumed silica, corn gluten feed, corngluten meal, dried distiller's grains, clay, vermiculite, diatamaciousearth, or milled corn, or any combinations thereof. In one variation,the carrier material is milled corn. In another variation, the carriermaterial is ground rice hulls. In yet another variation, the carriermaterial is ground oat hulls.

In certain variations, a syrup comprising the oligosaccharidecomposition is combined with a carrier material to produce the animalfeed pre-mix. In some variations, the syrup comprises theoligosaccharide composition and water, wherein the syrup has a finalsolids content of at least 40%, at least 45%, at least 50%, at least55%, at least 60%, at least 65%, at least 70%, at least 75%, between 40%and 75%, between 50% and 75%, or between 60 and 70% kg dry solids per kgof syrup. In one embodiment, the syrup comprises the oligosaccharidecomposition and water, wherein the syrup has a final solids content ofabout 65% kg dry solids per kg of syrup.

In some embodiments, the oligosaccharide composition is combined withthe carrier material to produce an animal feed pre-mix, wherein theanimal feed pre-mix is a dry powder. In some variations, the animal feedpre-mix is a dry, flowable powder. In certain variations, the animalfeed pre-mix has a final moisture content of less than 20 wt %, lessthan 15 wt %, less than 12 wt %, less than 10 wt %, or less than 5 wt %.In one variation, the animal feed pre-mix has a final moisture contentof less than 12 wt %, or less than 10 wt %.

In some variations, the oligosaccharide composition is combined with thecarrier material to produce a mixture, and the mixture is dried toproduce an animal feed pre-mix with the desired moisture content. Anysuitable method of drying may be used. For example, in certainembodiments the oligosaccharide composition is combined with the carriermaterial to produce a mixture, and the mixture is dried using a rotatingdrum drier to produce an animal feed pre-mix with the desired moisturecontent.

The animal feed pre-mix may comprise the oligosaccharide composition atany suitable concentration. In some embodiments, the animal feed pre-mixcomprises at least 1 wt %, at least 5 wt %, at least 10 wt %, at least15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least35 wt %, at least 40 wt %, at least 45 wt %, between 1 to 80 wt %,between 5 to 70 wt %, between 10 to 60 wt %, between 15 to 50 wt %, orbetween 20 to 50 wt % kg dry oligosaccharide composition per kg totalpremix, including moisture.

In some embodiments, the carrier material comprises copper and/or zinc.In certain variations, the carrier material comprises both copper andzinc. In certain variations, the carrier material comprises growthpromoting levels of copper and/or zinc. For example, in one variation,the carrier material comprises (i) between 10 ppm and 500 ppm copper;and/or (ii) between 10 ppm and 5000 ppm zinc.

In certain variations, the carrier material comprises an ionophore orother coccidiostat. In other variations, the carrier material does notcomprise an ionophore. In some variations, the carrier materialcomprises less than 1,000 ppm, less than 500 ppm, less than 100 ppm, orless than 50 ppm of an ionophore or other coccidiostat. In someembodiments, the ionophore is monensin, salinomycin, narasin, orlasolocid, or any combinations thereof.

In some embodiments, the carrier material does not comprise anantiobiotic. In certain variations, the carrier material comprises lessthan 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 50 ppm,less than 22 ppm, or less than 11 ppm of antibiotic. In someembodiments, the antibiotic is bacitracin, bacitracin methylenedisalicylate, bacitracin-zinc, virginiamycin, bambermycin, avilamycin,or efrotomycin, or any combinations thereof.

In certain variations, a carrier material is combined with anoligosaccharide composition to produce an animal feed pre-mix, whereinthe oligosaccharide composition has a distribution of glycosidic bondlinkages, as described above. Thus, the animal feed pre-mix may comprisean oligosaccharide composition, wherein the oligosaccharide compositionhas any distribution of glycosidic bond linkages described herein. Itshould be understood that the carrier material may also have adistribution of glycosidic bond linkages, and that in some embodimentsthe distribution may differ from the distribution of glycosidic bondlinkages of the oligosaccharide composition.

It should be understood that the animal feed pre-mix may comprise acarrier material as described herein and an oligosaccharide compositionas described herein, as if each and every combination were individuallylisted. For example, in some variations, provided herein is an animalfeed pre-mix comprising (i) a carrier material, and (ii) anoligosaccharide composition, wherein the oligosaccharide composition hasa glycosidic bond type distribution of at least 1 mol % α-(1,3)glycosidic linkages, and at least 1 mol % β-(1,3) glycosidic linkages,wherein at least 10 dry wt % of the oligosaccharide composition has adegree of polymerization of at least 3. In some variations, theoligosaccharide composition further has a glycosidic bond distrution ofat least 15 mol % β-(1,6) glycosidic linkages.

In other variations, provided herein is an animal feed pre-mixcomprising (i) a carrier material, and (ii) an oligosaccharidecomposition, wherein the oligosaccharide composition has a glycyosidicbond type distribution of less than 20 mol % α-(1,4) glycosidiclinkages, and less than 30 mol % α-(1,6) glycosidic linkages, wherein atleast 10 dry wt % of the oligosaccharide composition has a degree ofpolymerization of at least 3.

In other variations, provided herein is an animal feed pre-mixcomprising (i) a carrier material, and (ii) an oligosaccharidecomposition, wherein the oligosaccharide composition has a glycyosidicbond type distribution of between 0 to 15 mol % α-(1,2) glycosidiclinkages; between 0 to 30 mol % β-(1,2) glycosidic linkages; between 1to 30 mol % α-(1,3) glycosidic linkages; between 1 to 20 mol % β-(1,3)glycosidic linkages; and between 0 to 55 mol % β-(1,4) glycosidiclinkages. In some variations, the oligosaccharide composition furtherhas a bond distribution of between 15 to 55 mol % β-(1,6) glycosidiclinkages.

In another embodiment that may be combined with any of the foregoingembodiments, the oligosaccharide composition has a glycosidic bond typedistribution of less than 20 mol % α-(1,4) glycosidic linkages, and lessthan 30 mol % α-(1,6) glycosidic linkages. In still another embodiment,the animal feed pre-mix comprises at least 10 wt %, between 10 to 60 wt%, or between 20 to 50 wt % dry oligosaccharide composition per weightanimal feed pre-mix. In certain embodiments, at least 50 dry wt %, orbetween 65 and 80 dry wt % of the oligosaccharide composition has adegree of polymerization of at least 3. In some embodiments, themoisture content of the animal feed pre-mix is less than 20 wt %. Instill other variations, at least 50 dry wt % of the oligosaccharidecomposition comprises one or more gluco-oligosaccharides, or at least 50dry wt % of the oligosaccharide composition comprises one or moregluco-galacto-oligosaccharides.

Methods of Producing Animal Feed Compositions

The oligosaccharide compositions produced according to the methodsdescribed herein may be fed directly to animals, or may be combined witha base feed to produce animal feed compositions. Thus, in some aspects,provided is a method of producing an animal feed composition, by:combining the oligosaccharide composition produced according to any ofthe methods described herein with a base feed to produce an animal feedcomposition. Suitable base feed may include, for example, fodder,corn-soy based diets, or wheat-soy based diets. In some variations, theoligosaccharide composition is combined with a carrier material toproduce an animal feed pre-mix. The animal feed pre-mix may then becombined with a base feed to produce an animal feed composition. Thus,in some aspects, provided is a method of producing an animal feedpre-mix by: combining the oligosaccharide composition produced accordingto any of the methods described herein with a carrier material toproduce an animal feed pre-mix. In some variations, the method furthercomprises: combining the animal feed pre-mix with a base feed to producean animal feed composition.

In some embodiments, the oligosaccharide composition is combined with acarrier material to produce an animal feed pre-mix. This animal feedpre-mix may be fed directly to animals, or may be combined with a basefeed to produce an animal feed composition. In some variations, thepre-mix is produced in one location, shipped to a second location, andcombined with a base feed to produce an animal feed composition.

Use of Oligosaccharide Composition to Enhance Growth in Animals

In some aspects, provided is a method of enhancing growth of an animal,by:

-   -   providing feed to the animal, wherein the feed is made up of a        base feed, and an oligosaccharide composition; and    -   enhancing growth in the animal.

In some variations, the animal is poultry. In other variations, theanimal is swine. Any of the oligosaccharide compositions describedherein may be used in the foregoing method. For example, in oneembodiment, the oligosaccharide composition has a glycosidic bond typedistribution of: at least 1 mol % α-(1,3) glycosidic linkages; and atleast 1 mol % β-(1,3) glycosidic linkages. In another embodiment thatmay be combined with the foregoing embodiment, the oligosaccharidecomposition has a bond distribution of at least 15 mol % β-(1,6)glycosidic linkages. In still other embodiments, at least 10 dry wt % ofthe oligosaccharide composition has a degree of polymerization of atleast 3.

In another embodiment, the oligosaccharide composition is present in tehfeed at below 5,000 ppm, below 3,000 ppm, between 10 to 1,000 ppm, orbetween 10 to 500 ppm weight dry oligosaccharide composition per weightof the feed.

The oligosaccharide composition may be fed directly to the animal, beprocessed into an animal feed pre-mix, or incorporated into an animalfeed composition fed to the animal. In some embodiments, an animal fedthe oligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein may experience enhanced growth ascompared to an animal that is not fed the oligosaccharide composition,animal feed pre-mix, or animal feed composition over the same period oftime. In some embodiments, an animal population fed the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein may experience enhanced growth as compared to an animalpopulation that is not fed the oligosaccharide composition, animal feedpre-mix, or animal feed composition over the same period of timeEnhanced growth may include, for example, an increase in weight gain, adecrease in the food conversion ratio (FCR), an increase indigestibility of provided feed, an increase in released nutrients fromprovided feed, or a reduced mortality rate, or any combinations thereof.

In some embodiments, an animal population provided the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein may experience enhanced growth as compared to an animalpopulation that is not provided the oligosaccharide composition, animalfeed pre-mix, or animal feed composition Enhanced growth of the animalpopulation may include, for example, an increase in weight gain, anincrease in average daily feed intake, a decrease in the food conversionratio (FCR), an increase in digestibility of provided feed, an increasein released nutrients from provided feed, a reduced mortality rate, oran increase in animal uniformity, or any combinations thereof.

a) Weight Gain

In some embodiments, a subject animal that is fed the oligosaccharidecomposition, animal feed pre-mix, or the animal feed composition mayexperience an increase in weight gain, compared to a control animal thatis not fed the oligosaccharide composition, animal feed pre-mix, or theanimal feed composition. In certain embodiments, both the subject animaland the control animal comsume the same quantity of feed on a weightbasis, but the subject animal provided the oligosaccharide composition,animal feed pre-mix, or animal feed composition experiences an increasein weight gain compared to the control animal that is fed a diet thatdoes not include the oligosaccharide composition.

The weight gain of an animal may be determined by any suitable methodsknown in the art. For example, to determine weight gain of an animalthat is subjected to a feeding regimen of the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition, one ofskill in the art can measure the mass of an animal prior to the feedingregimen, measure the mass of the animal after the animal is fed theoligosaccharide composition, animal feed pre-mix, or animal feedcomposition, and determine the difference between those twomeasurements.

In some variations, the weight gain may be an average daily weight gain(also referred to as average daily gain (ADG)), an average weekly weightgain (AWG), or a final body weight gain (BWG).

Average Daily Weight Gain (or Average Daily Gain)

In some variations, providing an animal with an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition results inan increased average daily weight gain than an animal provided feedwithout the oligosaccharide composition. In some variations, providingan animal population with an oligosaccharide composition, animal feedpre-mix, or animal feed composition results in an increased averagedaily weight gain than an animal population provided feed without theoligosaccharide composition.

In one embodiment, the average daily weight gain for an animal is theweight gained each day by an individual animal, averaged over a givenperiod of time. In some variations, the average daily weight gain for ananimal population is the average daily weight gain for each individualanimal, averaged over the population; wherein the average daily weightgain is the weight gained each day by the individual animal, averagedover a given period of time. In yet other variations, the average dailyweight gain for an animal population is the total weight gained by thepopulation each day, divided by the number of individual animals in thepopulation, averaged over a given period of time. It should beunderstood that the daily weight gain or average daily weight gain maybe further averaged, for example to provide an average daily weight gainacross animal populations.

In certain embodiments, the animal is poultry, and the poultry providedan oligosaccharide composition, animal feed pre-mix, or animal feedcomposition has an average daily weight gain of at least 20 grams perday, at least 30 grams per day, at least 40 grams per day, at least 50grams per day, at least 60 grams per day, at least 70 grams per day, atleast 80 grams per day, at least 90 grams per day, between 20 to 100grams per day, between 20 to 80 grams per day, between 30 to 50 gramsper day, between 40 to 60 grams per day, between 50 to 70 grams per day,or between 70 to 90 grams per day. In one embodiment, the animal ispoultry, and the poultry provided an oligosaccharide composition, animalfeed pre-mix, or animal feed composition has an average daily weightgain of at least 50 grams per day. In certain embodiments, the poultryprovided an oligosaccharide composition, animal feed pre-mix, or animalfeed composition has an average daily weight gain of at least 1%, atleast 2%, at least 3%, at least 4%, at least 5%, at least 6%, at least8%, at least 9%, at least 10%, at least 11%, at least 12%, between 1 to10%, between 2 to 8%, or between 3 to 5% greater than the average dailyweight gain of poultry provided a diet that does not include theoligosaccharide composition.

In certain embodiments, the animal is poultry, and the poultry isbetween 0 to 14 days of age, and the average daily weight gain is atleast 30 grams, at least 40 grams, or at least 50 grams per day.

In other embodiments, the animal is poultry, the poultry is between 14to 28 days of age, and teh average daily weight gain is at least 70grams, at least 80 grams, or at least 90 grams per day.

In still other embodiments, the animal is poultry, the poultry isabetween 29 to 35 days of age, and the average daily weight gain is atleast 50 grams, at least 60 grams, or at least 70 grams per day.

In some variations that may be combined with the foregoing, the animalis poultry, and the animal feed composition is poultry feed, wherein theoligosaccharide composition, poultry feed pre-mix, or poultry feedcomposition increases average daily gain in poultry by up to about 10%,or about 5%, or between 1% and 10%, between 2% and 10%, between 3% and10%, between 4% and 10%, between 5% and 10%, between 2% and 5%, between2% and 6%, between 2% and 7%, between 2% and 8%, between 2% and 9%, orbetween 1% and 5%, when fed to the poultry as compared to poultry fed afeed composition without the oligosaccharide composition.

In certain variations, the poultry suffers from a disease or a disorder,or is raised in a challenged environment, wherein the oligosaccharidecomposition, poultry feed pre-mix, or poultry feed composition increasesaverage daily gain in poultry by up to about 30%, about 25%, about 20%,about 15%, about 10%, or about 5%, or between 1% and 30%, between 5% and30%, between 10% and 30%, between 5% and 20%, between 10% and 20%,between 1% and 20%, between 1% and 15%, between 1% and 10%, between 2%and 10%, between 3% and 10%, between 4% and 10%, between 5% and 10%,between 2% and 5%, between 2% and 6%, between 2% and 7%, between 2% and8%, between 2% and 9%, or between 1% and 5%, when fed to the poultry ascompared to poultry fed a feed composition without the oligosaccharidecomposition.

In some variations that may be combined with the foregoing, the animalis swine, and the animal feed composition is swine feed, wherein theoligosaccharide composition, swine feed pre-mix, or swine feedcomposition increases average daily gain in swine by up to about 15%,about 10%, or about 5%, or between 1% and 15%, between 2% and 15%,between 3% and 15%, between 4% and 15%, between 5% and 15%, between 10%and 15%, between 1% and 10%, between 2% and 10%, between 3% and 10%,between 4% and 10%, between 5% and 10%, between 2% and 5%, between 2%and 6%, between 2% and 7%, between 2% and 8%, between 2% and 9%, orbetween 1% and 5%, when fed to swine as compared to swine fed a feedcomposition without the oligosaccharide composition.

In certain variations, the swine suffers from a disease or a disorder,or is raised in a challenged environment, wherein the oligosaccharidecomposition, swine feed pre-mix, or swine feed composition increasesaverage daily gain in swine by up to about 40%, about 35% about 30%,about 25%, about 20%, about 15%, about 10%, or about 5%, or between 1%and 40%, between 5% and 40%, between 10% and 40%, between 15% and 40%,between 20% and 40%, between 25% and 40%, between 30% and 40%, between1% and 30%, between 5% and 30%, between 10% and 30%, between 5% and 20%,between 10% and 20%, between 1% and 20%, between 1% and 15%, between 1%and 10%, between 2% and 10%, between 3% and 10%, between 4% and 10%,between 5% and 10%, between 2% and 5%, between 2% and 6%, between 2% and7%, between 2% and 8%, between 2% and 9%, or between 1% and 5%, when fedto swine as compared to swine fed a feed composition without theoligosaccharide composition.

In certain embodiments, the animal is swine, and the swine provided anoligosaccharide composition, swine feed pre-mix, or swine feedcomposition has an average daily weight gain of at least 1%, at least2%, at least 3%, at least 4%, at least 5%, at least 6%, at least 8%, atleast 9%, at least 10%, at least 11%, at least 12%, between 1 to 10%,between 2 to 8%, or between 3 to 5% greater than the average dailyweight gain of swine provided a diet that does not include theoligosaccharide composition.

Average Weekly Weight Gain

In some variations, providing an animal with an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition results inan increased average weekly weight gain than an animal provided feedwithout the oligosaccharide composition. In some variations, providingan animal population with an oligosaccharide composition, animal feedpre-mix, or animal feed composition results in an increased averageweekly weight gain than an animal population provided feed without theoligosaccharide composition.

In one embodiment, the average weekly weight gain for an animal is theweight gained each week by an individual animal, averaged over a givenperiod of time. In some variations, the average weekly weight gain foran animal population is the average weekly weight gain for eachindividual animal, averaged over the population; wherein the averageweekly weight gain is the weight gained each week by the individualanimal, averaged over a given period of time. In yet other variations,the average weekly weight gain for an animal population is the totalweight gained by the population each week, divided by the number ofindividual animals in the population, averaged over a given period oftime. It should be understood that the average weekly weight gain may befurther averaged, for example to provide an average weekly weight gainacross animal populations.

In certain embodiments, the animal is poultry, and poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition has an average weekly weight gain of at least 100 grams perweek, at least 200 grams per week, at least 300 grams per week, at least400 grams per week, at least 500 grams per week, at least 600 grams perweek, at least 700 grams per week, at least 800 grams per week, between100 to 800 grams per week, between 100 to 400 grams per week, between300 to 600 grams per week, between 500 to 800 grams per week, or between350 to 550 grams per week. In one embodiment, poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition has an average weekly weight gain of at least 400 grams perweek. In certain embodiments, poultry provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition has anaverage weekly weight gain of at least 1%, at least 2%, at least 3%, atleast 4%, at least 5%, at least 6%, at least 8%, at least 9%, at least10%, at least 11%, at least 12%, between 1 to 10%, between 2 to 8%, orbetween 3 to 5% greater than the average weekly weight gain of poultryprovided a diet that does not include the oligosaccharide composition.

In certain embodiments, the animal is swine, and swine provided anoligosaccharide composition, swine feed pre-mix, or swine feedcomposition has an average weekly weight gain of at least 1%, at least2%, at least 3%, at least 4%, at least 5%, at least 6%, at least 8%, atleast 9%, at least 10%, at least 11%, at least 12%, between 1 to 10%,between 2 to 8%, or between 3 to 5% greater than the average weeklyweight gain of swine provided a diet that does not include theoligosaccharide composition.

Final Body Weight Gain

In some variations, providing an animal with an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition results inan increased final body weight gain than an animal provided feed withoutthe oligosaccharide composition. In some variations, providing an animalpopulation with an oligosaccharide composition, animal feed pre-mix, oranimal feed composition results in an increased average final bodyweight gain than an animal population provided feed without theoligosaccharide composition.

In some variations, providing an animal or animal population with anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition results in a final body weight gain or average final bodyweight gain that is closer to the performance target maximum than ananimal or animal population that is provided feed without theoligosaccharide composition. The performance target maximum generallyrefers to the highest practical body weight gain observed for a giventype of animal and breed under ideal growing conditions, ideal animalhealth, and ideal dietary nutrition.

In one embodiment, the final body weight gain is the quantity of weightan individual animal gains over a period of time. For example, in oneembodiment, the total body weight gain is the quantity of weight anindividual animal gains from 0 days of age until the final weight takenprior to processing of the animal, or the final weight taken on the dayof processing of the animal. For example, in one embodiment, the day 0to 28 total body weight gain for an animal is the quantity of weight anindividual animal gains from 0 days of age until 28 days of age.

In another embodiment, the average total body weight gain is thequantity of weight an individual animal gains over a period of time,averaged across an animal population. For example, in one embodiment,the average total body weight gain is the quantity of weight anindividual animal gains from 0 days of age until the final weight takenprior to processing of the animal, or the final weight taken on the dayof processing of the animal, averaged across the animal population. Inyet another embodiment, the average total body weight gain is thequantitity of weight an animal population gains over a period of time,divided by the number of individual animals in the population. Forexample, in one embodiment, the average total body weight gain is thequantity of weight an animal population gains from 0 days of age untilthe final weight taken prior to processing of the animal population, orthe final weight taken on the day of processing of the animal, dividedby the number of individual animals in the population.

It should be understood that the values for total body weight gain andaverage total body weight gain can be further averaged. For example, theaverage total body weight gain for different populations of the sametype of animal may be averaged to obtain an average total body weightgain across populations.

In certain embodiments, the animal is poultry, and poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition has a final body weight gain of at least 3 kg, at least 2.5kg, at least 2 kg, at least 1.5 kg, at least 1 kg, between 1 to 3 kg, orbetween 1.5 to 2.5 kg. In one embodiment, poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition has a final body weight gain of at least 2 kg. In certainembodiments, poultry provided an oligosaccharide composition, animalfeed pre-mix, or animal feed composition has a final body weight gain ofat least 1%, at least 2%, at least 3%, at least 4%, at least 5%, atleast 6%, at least 8%, at least 9%, at least 10%, at least 11%, at least12%, between 1 to 10%, between 2 to 8%, or between 3 to 5% greater thanthe final body weight gain of poultry provided a diet that does notinclude the oligosaccharide composition. In certain embodiments, poultryprovided an oligosaccharide composition, animal feed pre-mix, or animalfeed composition has a final body weight gain of at least 0.01 kg, atleast 0.02 kg, at least 0.03 kg, at least 0.04 kg, at least 0.05 kg, atleast 0.06 kg, at least 0.07 kg, at least 0.08 kg, at least 0.09 kg, atleast 0.1 kg, between 0.01 to 0.1 kg, between 0.03 to 0.07 kg, orbetween 0.04 to 0.06 kg greater than the final body weight gain ofpoultry provided a diet that does not include the oligosaccharidecomposition.

In certain embodiments, the animal is poultry, and poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition has an average final body weight gain of at least 3 kg, atleast 2.5 kg, at least 2 kg, at least 1.5 kg, at least 1 kg, between 1to 3 kg, or between 1.5 to 2.5 kg. In one embodiment, poultry providedan oligosaccharide composition, animal feed pre-mix, or animal feedcomposition has an average final body weight gain of at least 2 kg. Incertain embodiments, poultry provided an oligosaccharide composition,animal feed pre-mix, or animal feed composition has an average finalbody weight gain of at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 8%, at least 9%, at least 10%, atleast 11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3to 5% greater than the average final body weight gain of poultryprovided a diet that does not include the oligosaccharide composition.In certain embodiments, poultry provided an oligosaccharide composition,animal feed pre-mix, or animal feed composition has an average finalbody weight gain of at least 0.01 kg, at least 0.02 kg, at least 0.03kg, at least 0.04 kg, at least 0.05 kg, at least 0.06 kg, at least 0.07kg, at least 0.08 kg, at least 0.09 kg, at least 0.1 kg, between 0.01 to0.1 kg, between 0.03 to 0.07 kg, or between 0.04 to 0.06 kg greater thanthe average final body weight gain of poultry provided a diet that doesnot include the oligosaccharide composition.

In some embodiments, the animal is poultry, and the poultry is between 0to 14 days of age, between 15 to 28 days of age, between 29 to 35 daysof age, between 0 to 42 days of age, between 0 to 6 weeks of age, orbetween 0 to 6.5 weeks of age. In some embodiments, the starter phase is0 to 14 days of age, the grower phase is 15 to 28 days of age, and thefinisher phase is 29 to 35 days of age. In other embodiments, thestarter phase is 0 to 14 days of age, the grower phase is 15 to 35 daysof age, and the finisher phase is 36 to 42 days of age. In yet otherembodiments, the starter phase is 0 to 14 days of age, the grower phaseis 15 to 39 days of age, and the finisher phase is 40 to 46 days of age.It should be understood that the length of the starter phase, growingphase, and finisher phase for poultry may change depending on theintended use of the poultry, or the poultry product. For example, insome embodiments the length of the starter phase, grower phase, andfinisher phase may be different if the intended use of the poultry is asa broiler chicken, compared to processing for tray-pack chicken meat.

In some embodiments that may be combined with any of the foregoingembodiments, the poultry is an individual poultry, while in otherembodiments the poultry is a poultry population.

In certain embodiments, swine provided an oligosaccharide composition,swine feed pre-mix, or swine feed composition has a final body weightgain of at least 1%, at least 2%, at least 3%, at least 4%, at least 5%,at least 6%, at least 8%, at least 9%, at least 10%, at least 11%, atleast 12%, between 1 to 10%, between 2 to 8%, or between 3 to 5% greaterthan the final body weight gain of swine provided a diet that does notinclude the oligosaccharide composition.

In certain embodiments, swine provided an oligosaccharide composition,swine feed pre-mix, or swine feed composition has an average final bodyweight gain of at least 1%, at least 2%, at least 3%, at least 4%, atleast 5%, at least 6%, at least 8%, at least 9%, at least 10%, at least11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3 to 5%greater than the average final body weight gain of swine provided a dietthat does not include the oligosaccharide composition.

In some embodiments that may be combined with any of the foregoingembodiments, the swine is an individual swine, while in otherembodiments the swine is a swine population.

b) Average Daily Feed Intake

In certain variations, providing an animal with an oligosaccharidecompositions, animal feed pre-mix, or animal feed composition asdescribed herein results in an increased average daily feed intake, ascompared to an animal provided feed that does not include theoligosaccharide composition.

Average daily feed intake (ADFI) refers to the average mass of feedconsumed by an animal over a specified period of time. In certainvariations, the average daily feed intake is measured by dispensing aknown mass of feed to a group of a fixed number of animals, allowing theanimals in the group to consume the dispensed feed freely (ad libidum)for a specified number of days, weighing the mass of unconsumed feed atthe end of the period, and calculating the average daily feed intake(ADFI) as the difference between the dispensed feed mass minus theresidual feed mass, divided by the number of animals in the group, anddivided by the number of days in the period. In other variations, theaverage daily feed intake may be corrected for any animals that die orare culled from the group, using methods that are known to one skilledin the art.

In some variations, the animal is poultry, and the animal feedcomposition is poultry feed, wherein the oligosaccharide composition,poultry feed pre-mix, or poultry feed composition feed increases averagedaily feed intake by up to about 10%, or about 5%, or between 1% and10%, between 2% and 10%, between 3% and 10%, between 4% and 10%, between5% and 10%, between 2% and 5%, between 2% and 6%, between 2% and 7%,between 2% and 8%, between 2% and 9%, or between 1% and 5%, when fed topoultry as compared to poultry fed a feed composition without theoligosaccharide composition.

In certain variations, the poultry suffers from a disease or is raisedin a challenged environment, wherein the oligosaccharide composition,poultry feed pre-mix, or poultry feed composition increases averagedaily feed intake by up to about 30%, about 25%, about 20%, about 15%,about 10%, or about 5%, or between 1% and 30%, between 5% and 30%,between 10% and 30%, between 5% and 20%, between 10% and 20%, between 1%and 20%, between 1% and 15%, between 1% and 10%, between 2% and 10%,between 3% and 10%, between 4% and 10%, between 5% and 10%, between 2%and 5%, between 2% and 6%, between 2% and 7%, between 2% and 8%, between2% and 9%, or between 1% and 5%, when fed to poultry as compared topoultry fed a feed composition without the oligosaccharide composition

In some variations that may be combined with the foregoing, the animalis swine, and the animal feed composition is swine feed, wherein theoligosaccharide composition, swine feed pre-mix, or swine feedcomposition increases average daily feed intake by up to about 15%,about 10%, or about 5%, or between 1% and 15%, between 2% and 15%,between 3% and 15%, between 4% and 15%, between 5% and 15%, between 10%and 15%, between 1% and 10%, between 2% and 10%, between 3% and 10%,between 4% and 10%, between 5% and 10%, between 2% and 5%, between 2%and 6%, between 2% and 7%, between 2% and 8%, between 2% and 9%, orbetween 1% and 5%, when fed to swine as compared to swine fed a feedcomposition without the oligosaccharide composition.

In certain variations, the swine suffers from a disease or is raised ina challenged environment, wherein the oligosaccharide composition, swinefeed pre-mix, or swine feed composition increases average daily feedintake by up to about 40%, about 35% about 30%, about 25%, about 20%,about 15%, about 10%, or about 5%, or between 1% and 40%, between 5% and40%, between 10% and 40%, between 15% and 40%, between 20% and 40%,between 25% and 40%, between 30% and 40%, between 1% and 30%, between 5%and 30%, between 10% and 30%, between 5% and 20%, between 10% and 20%,between 1% and 20%, between 1% and 15%, between 1% and 10%, between 2%and 10%, between 3% and 10%, between 4% and 10%, between 5% and 10%,between 2% and 5%, between 2% and 6%, between 2% and 7%, between 2% and8%, between 2% and 9%, or between 1% and 5%, when fed to swine ascompared to swine fed a feed composition without the oligosaccharidecomposition.

c) Yield of Animal Product

In certain variations, providing an animal with an oligosaccharidecompositions, animal feed pre-mix, or animal feed composition asdescribed herein results in an increased yield of animal product, ascompared to an animal provided feed that does not include theoligosaccharide composition. In some embodiments, the animal provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition yields at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 7%, at least 8%, at least 9%, atleast 10%, between 1 to 10%, between 4 to 10%, between 6 to 10%, orbetween 2 to 8% more animal product compared to an animal provided feedthat does nto include the oligosaccharide composition. For example, insome embodiments, the animal product is the meat of the animal, and ananimal provided an oligosaccharide composition as described hereinyields a greater quantity of meat compared to an animal that is notprovided the oligosaccharide composition. In some embodiments, providingan animal population the oligosaccharide composition, animal feedpre-mix, or animal feed composition results in an increased averageyield of animal product, as compared to an animal population providedfeed that does not include the oligosaccharide composition. In somevariations, the average animal product yield is the quantity of animalproduct yielded from each individual animal, averaged across the animalpopulation.

In some embodiments, the animal product is the meat of an animal (e.g.,that may be sold to consumers, processed to produce a food product, orconsumed by a human) In certain embodiments, the animal is poultry, andthe animal product is a poultry eviscerated carcass, leg meat from apoultry eviscerated carcass, breast meat from a poultry evisceratedcarcass, drumstick meat from a poultry eviscerated carcass, fat from apoultry eviscerated carcass, breast meat from a poultry deboned carcass,or leg meat from a poultry deboned carcass. In other embodiments, theanimal is poultry, and the animal product is white meat, breast meatfilets, and breast meat tenders. In another embodiement, the animal ispoultry and the product is tray-pack chicken meat. In yet anotherembodiment, the animal is poultry and the product is whole bird withoutgiblets (WOG).

In some embodiments, the yield of animal product is the yield obtainedfrom an individual animal. In some embodiments, the average yield ofanimal product is the yield obtained from each individual animal in ananimal population, averaged across the population. In yet anotherembodiment, the average yield of animal product is the total yield ofanimal product yielded from an animal population, divided by the numberof individual animals in the animal population.

In some variations, the animal is poultry, the yield of leg meat from apoultry eviscerated carcass is at least 6%, at least 8%, at least 10%,at least 12%, between 6 to 12%, between 8 to 12%, between 10 to 18%,between 12 to 16%, or between 12 to 14% of live weight for poultryprovided an oligosaccharide compositions, animal feed pre-mix, or animalfeed composition. In certain variations, the yield of leg meat from apoultry eviscerated carcass from poultry provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein is at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 8%, at least 9%, at least 10%, atleast 11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3to 5% greater than for poultry provided a diet that does not include theoligosaccharide composition.

In some variations, the animal is poultry, and the average yield of legmeat from a poultry eviscerated carcass is at least 6%, at least 8%, atleast 10%, at least 12%, between 6 to 12%, between 8 to 12%, between 10to 18%, between 12 to 16%, or between 12 to 14% of live weight forpoultry provided an oligosaccharide compositions, animal feed pre-mix,or animal feed composition. In certain variations, the average yield ofleg meat from a poultry eviscerated carcass from poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is at least 1%, at least 2%, at least3%, at least 4%, at least 5%, at least 6%, at least 8%, at least 9%, atleast 10%, at least 11%, at least 12%, between 1 to 10%, between 2 to8%, or between 3 to 5% greater than for poultry provided a diet thatdoes not include the oligosaccharide composition.

In some variations, the animal is poultry, and the yield of breast meatfrom a poultry eviscerated carcass is at least 10%, at least 12%, atleast 15%, at least 16%, at least 18%, at least 20%, at least 22%, atleast 24%, at least 28%, between 10 to 18%, between 12 to 16%, between18 to 29%, between 20 to 27%, or between 20 to 25% of live weight forpoultry provided an oligosaccharide compositions, animal feed pre-mix,or animal feed composition. In certain variations, the yield of breastmeat from a poultry eviscerated carcass from poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is at least 1%, at least 2%, at least3%, at least 4%, at least 5%, at least 6%, at least 8%, at least 9%, atleast 10%, at least 11%, at least 12%, between 1 to 10%, between 2 to8%, or between 3 to 5% greater than for poultry provided a diet thatdoes not include the oligosaccharide composition.

In some variations, the animal is poultry, and the average yield ofbreast meat from a poultry eviscerated carcass is at least 10%, at least12%, at least 15%, at least 16%, at least 18%, at least 20%, at least22%, at least 24%, at least 28%, between 10 to 18%, between 12 to 16%,between 18 to 29%, between 20 to 27%, or between 20 to 25% of liveweight for poultry provided an oligosaccharide compositions, animal feedpre-mix, or animal feed composition. In certain variations, the averageyield of breast meat from a poultry eviscerated carcass from poultryprovided an oligosaccharide composition, animal feed pre-mix, or animalfeed composition as described herein is at least 1%, at least 2%, atleast 3%, at least 4%, at least 5%, at least 6%, at least 8%, at least9%, at least 10%, at least 11%, at least 12%, between 1 to 10%, between2 to 8%, or between 3 to 5% greater than for poultry provided a dietthat does not include the oligosaccharide composition.

In some variations, the animal is poultry, and the yield of drumstickmeat from a poultry eviscerated carcass is at least 5%, at least 7%, atleast 8%, at least 9%, at least 10%, at least 11%, at least 12%, between5 to 14%, between 7 to 10%, between 7 to 15%, between 9 to 13%, orbetween 9 to 11% of live weight for poultry provided an oligosaccharidecompositions, animal feed pre-mix, or animal feed composition. Incertain variations, the yield of drumstick meat from a poultryeviscerated carcass from poultry provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein is at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 8%, at least 9%, at least 10%, atleast 11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3to 5% greater than for poultry provided a diet that does not include theoligosaccharide composition.

In some variations, the animal is poultry, and the average yield ofdrumstick meat from a poultry eviscerated carcass is at least 5%, atleast 7%, at least 8%, at least 9%, at least 10%, at least 11%, at least12%, between 5 to 14%, between 7 to 10%, between 7 to 15%, between 9 to13%, or between 9 to 11% of live weight for poultry provided anoligosaccharide compositions, animal feed pre-mix, or animal feedcomposition. In certain variations, the average yield of drumstick meatfrom a poultry eviscerated carcass from poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is at least 1%, at least 2%, at least3%, at least 4%, at least 5%, at least 6%, at least 8%, at least 9%, atleast 10%, at least 11%, at least 12%, between 1 to 10%, between 2 to8%, or between 3 to 5% greater than for poultry provided a diet thatdoes not include the oligosaccharide composition.

In some variations, the animal is poultry, and the yield of breast meatfrom a poultry deboned carcass is at least 14%, at least 16%, at least18%, at least 20%, at least 22%, at least 24%, between 14 to 16%,between 18 to 30%, between 20 to 28%, or between 20 to 26% of liveweight for poultry provided an oligosaccharide compositions, animal feedpre-mix, or animal feed composition. In certain variations, the yield ofbreast meat from a poultry deboned carcass from poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is at least 1%, at least 2%, at least3%, at least 4%, at least 5%, at least 6%, at least 8%, at least 9%, atleast 10%, at least 11%, at least 12%, between 1 to 10%, between 2 to8%, or between 3 to 5% greater than for poultry provided a diet thatdoes not include the oligosaccharide composition.

In some variations, the animal is poultry, and the average yield ofbreast meat from a poultry deboned carcass is at least 14%, at least16%, at least 18%, at least 20%, at least 22%, at least 24%, between 14to 16%, between 18 to 30%, between 20 to 28%, or between 20 to 26% oflive weight for poultry provided an oligosaccharide compositions, animalfeed pre-mix, or animal feed composition. In certain variations, theaverage yield of breast meat from a poultry deboned carcass from poultryprovided an oligosaccharide composition, animal feed pre-mix, or animalfeed composition as described herein is at least 1%, at least 2%, atleast 3%, at least 4%, at least 5%, at least 6%, at least 8%, at least9%, at least 10%, at least 11%, at least 12%, between 1 to 10%, between2 to 8%, or between 3 to 5% greater than for poultry provided a dietthat does not include the oligosaccharide composition.

In some variations, the animal is poultry, and the yield of leg meatfrom a poultry deboned carcass is at least 6%, at least 8%, at least10%, at least 12%, at least 14%, at least 16%, at least 18%, between 6to 18%, between 8 to 16%, between 12 to 21%, between 14 to 19%, orbetween 14 to 17% of live weight for poultry provided an oligosaccharidecompositions, animal feed pre-mix, or animal feed composition. Incertain variations, the yield of leg meat from a poultry deboned carcassfrom poultry provided an oligosaccharide composition, animal feedpre-mix, or animal feed composition as described herein is at least 1%,at least 2%, at least 3%, at least 4%, at least 5%, at least 6%, atleast 8%, at least 9%, at least 10%, at least 11%, at least 12%, between1 to 10%, between 2 to 8%, or between 3 to 5% greater than for poultryprovided a diet that does not include the oligosaccharide composition.

In some variations, the animal is poultry, and the average yield of legmeat from a poultry deboned carcass is at least 6%, at least 8%, atleast 10%, at least 12%, at least 14%, at least 16%, at least 18%,between 6 to 18%, between 8 to 16%, between 12 to 21%, between 14 to19%, or between 14 to 17% of live weight for poultry provided anoligosaccharide compositions, animal feed pre-mix, or animal feedcomposition. In certain variations, the average yield of leg meat from apoultry deboned carcass from poultry provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein is at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 8%, at least 9%, at least 10%, atleast 11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3to 5% greater than for poultry provided a diet that does not include theoligosaccharide composition.

In some variations, the animal is poultry, and the yield of fat from apoultry eviscerated carcass is at least 0.1%, at least 0.2%, at least0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%, atleast 0.8%, at least 0.9%, at least 1%, at least 1.2%, at least 1.4%, atleast 1.6%, between 0.1 to 2%, between 0.2 to 1%, between 0.5 to 2%, orbetween 0.3 to 0.7% of live weight for poultry provided anoligosaccharide compositions, animal feed pre-mix, or animal feedcomposition. In certain variations, the yield of fat from a poultryeviscerated carcass from poultry provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein is at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 8%, at least 9%, at least 10%, atleast 11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3to 5% greater than for poultry provided a diet that does not include theoligosaccharide composition.

In some variations, the animal is poultry, and the average yield of fatfrom a poultry eviscerated carcass is at least 0.1%, at least 0.2%, atleast 0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%,at least 0.8%, at least 0.9%, at least 1%, at least 1.2%, at least 1.4%,at least 1.6%, between 0.1 to 2%, between 0.2 to 1%, between 0.5 to 2%,or between 0.3 to 0.7% of live weight for poultry provided anoligosaccharide compositions, animal feed pre-mix, or animal feedcomposition. In certain variations, the average yield of fat from apoultry eviscerated carcass from poultry provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein is at least 1%, at least 2%, at least 3%, at least 4%,at least 5%, at least 6%, at least 8%, at least 9%, at least 10%, atleast 11%, at least 12%, between 1 to 10%, between 2 to 8%, or between 3to 5% greater than for poultry provided a diet that does not include theoligosaccharide composition.

In some variations, the animal is poultry, and the yield of a poultryeviscerated carcass is at least 50%, at least 55%, at least 60%, atleast 65%, at least 70%, at least 75%, at least 80%, at least 85%, atleast 90%, between 50 to 95%, between 60 to 85%, or between 65 to 75% oflive weight for poultry provided an oligosaccharide compositions, animalfeed pre-mix, or animal feed composition. In certain variations, theyield of a poultry eviscerated carcass from poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is at least 1%, at least 2%, at least3%, at least 4%, at least 5%, at least 6%, at least 8%, at least 9%, atleast 10%, at least 11%, at least 12%, between 1 to 10%, between 2 to8%, or between 3 to 5% greater than for poultry provided a diet thatdoes not include the oligosaccharide composition.

In some variations, the animal is poultry, and the average yield of apoultry eviscerated carcass is at least 50%, at least 55%, at least 60%,at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, atleast 90%, between 50 to 95%, between 60 to 85%, or between 65 to 75% oflive weight for poultry provided an oligosaccharide compositions, animalfeed pre-mix, or animal feed composition. In certain variations, theaverage yield of a poultry eviscerated carcass from poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is at least 1%, at least 2%, at least3%, at least 4%, at least 5%, at least 6%, at least 8%, at least 9%, atleast 10%, at least 11%, at least 12%, between 1 to 10%, between 2 to8%, or between 3 to 5% greater than for poultry provided a diet thatdoes not include the oligosaccharide composition.

Methods for deboning a poultry carcass are well known to one skilled inthe art of poultry processing. It should be understood that meat yieldedfrom poultry may be measured, for example, as the ratio of the mass ofrecovered meat to the final weight of the bird prior to processing.

In some variations, the animal is poultry, and the poultry is at least35 days old, at least 42 days old, at least 6 weeks old, at least 6.5weeks old before the poultry is processed to produce a poultryeviscerated carcass, poultry deboned carcass, white meat, breast meatfilets, and breast meat tenders, tray-pack chicken meat, whole birdwithout giblets (WOG), or meat as described above.

In other variations, the animal is poultry, and the animal product iseggs.

In some embodiments, the animal is swine, and the swine product is themeat of swine (e.g., that may be sold to consumers, processed to producea food product, or consumed by a human). In some embodiments, the yieldof swine product is the yield obtained from an individual swine. In someembodiments, the average yield of swine product is the yield obtainedfrom each individual swine in a swine population, averaged across thepopulation. In yet another embodiment, the average yield of swineproduct is the total yield of swine product yielded from swinepopulation, divided by the number of individual swine in the swinepopulation.

In certain variations, an animal or animal population provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition has a higher average daily weight gain, higher averageweekly weight gain, higher final body weight gain, higher average finalbody weight gain, or increased average yield of animal product, or anycombinations thereof, than an animal or animal population provided adiet that does not include the oligosaccharide composition, but whichdoes include one or more antibiotics, one or more ionophores, solublecorn fiber, modified wheat starch, or yeast mannan, or any combinationsthereof.

A person of skill in the art would recognize that the maximumtheoretical weight gain may be different for different types of animalsand may be different for different breeds of the same type of animal(for example, different types of broiler chickens, or different types ofswine).

In some embodiments, the animal is poultry. In some embodiments that maybe combined with any of the foregoing embodiments, the poultry is anindividual poultry, while in other embodiments the poultry is a poultrypopulation. In other embodiments, the animal is swine. In someembodiments that may be combined with any of the foregoing embodiments,the swine is an individual swine, while in other embodiments the swineis a swine population.

d) Feed Conversion Ratio

In some variations, an animal provided an oligosaccharide composition,animal feed pre-mix, or animal feed composition as described herein hasa lower feed conversion ratio compared to an animal provided a diet thatdoes not include the oligosaccharide composition. In some variations,feed conversion ratio (FCR) refers to the ratio of feed mass input (forexample, consumed by the animal) to the animal output, wherein theanimal output is the target animal product. For example, the animaloutput for dairy animals is milk, whereas the animal output for animalsraised for meat is body mass.

In some variations, the animal is raised for meat, and the target animaloutput is body mass. Thus, in some variations, the FCR refers to theratio of the weight of feed consumed compared to the final body weightof the animal prior to processing. In some variations, the FCR refers tothe ratio of the weight of feed consumed compared to the final bodyweight gain of the animal prior to processing. It should be understoodthat FCR may be measured for an animal or population of animals overdifferent time periods. For example, in some variations, the FCR is anFCR over the entire lifetime of the animal. In other variations, the FCRis a daily FCR, or a weekly FCR, or a cumulative FCR measured up until aparticular moment in time (for example, a particular day).

A person of skill in the art would recognize that the performance targetminimum feed conversion ratio (optimal FCR) may be different fordifferent types of animal, and may be different for different breeds ofone type animal (for example, different breeds of broiler chickens, ordifferent breeds of swine). The performance target minimum feedconversion ratio may also be different depending on age of the animal(for example, chickens or swine in a grower phase compared to a finisherphase), or the sex of the animal. It should be clear that the optimalFCR may be different depending on any combination of these factors.

Performance target minimum generally refers to the lowest feedefficiency observed for a given animal and breed under ideal growingconditions, ideal animal health, and ideal dietary nutrition. It is wellknown to one skilled in the art that under common growing conditions, ananimal may not achieve the performance target minimum FCR. An animal maynot achieve its performance target minimum FCR due to a variety ofhealth, nutrition, environmental, and/or community influences. An animalmay not achieve its performance target minimum FCR when raised in achallenged environment, which may include, for example, environmentalpathogenic stress, excessive environmental temperature (heat stress),excessive environmental humidity, crowding, or other social interactioneffects, such as difficulty accessing feed or drinking water. In someembodiments, an animal may not achieve its performance target minimumFCR due to disease or environmental pathogenic stress. In otherembodiments, an animal may not achieve its performance target minimumFCR due to excessive environmental temperature (heat stress), orexcessive environmental humidity. In yet other embodiments, an animalmay not achieve its performance target minimum FCR due to crowding, orother social interaction effects, such as difficulty accessing feed ordrinking water.

In some variations, an animal provided a diet which does not include theoligosaccharide composition as described herein has an FCR that is atleast 1% higher than the performance target minimum, at least 2% higherthan the performance target minimum, at least 3% higher than theperformance target minimum, at least 4% higher than the performancetarget minimum, at least 5% higher than the performance target minimium,at least 6% higher than the performance target minimum, at least 7%higher than the performance target minimum, at least 8% higher than theperformance target minimum, at least 9% higher than the performancetarget minimum, or at least 10% higher than the performance targetminimum FCR. In certain embodiments, an animal provided a diet wich doesnot include an oligosaccharide composition as described herein has anFCR that is 1% to 10% higher than the performance target minimum, 2% to10% higher than the performance target minimum, or 5% to 10% higher thanthe performance target minimum.

In some variations, an animal provided an oligosaccharide composition,animal feed pre-mix, or animal feed composition as described herein hasan FCR that is closer to the performance target minimum compared to ananimal provided a diet that does not include the oligosaccharidecomposition. In particular embodiments, the animal provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein has an FCR that is between 0 to 10%higher than the performance target minimum, between 0 to 5% higher thanthe performance target minimum, or between 0 to 2% higher than theperformance target minimum.

In some variations, an animal provided an oligosaccharide composition,animal feed pre-mix, or animal feed composition as described herein hasa lower feed conversion ratio compared to an animal provided a diet thatdoes not include the oligosaccharide composition. For example, incertain variations, the animal provided a diet comprising theoligosaccharide composition consumes less food but has the same animaloutput as compared to an animal provided a diet that does not includethe oligosaccharide composition. In other variations, the animalprovided a diet comprising the oligosaccharide composition consumes thesame amount of food but has a higher animal output as compared to ananimal provided a diet that does not include the oligosaccharidecomposition. In yet other variations, the animal provided a dietcomprising the oligosaccharide composition consumes less food and has ahigher animal output as compared to an animal provided a diet that doesnot include the oligosaccharide composition.

In some variations, the FCR of an animal provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein is reduced at least 1%, at least 2%, at least 4%, atleast 6%, at least 8%, at least 10%, at least 12%, between 1 to 10%,between 4 to 10%, between 1 to 8%, between 4 to 8%, between 1 to 6%, orbetween 4 to 6% as compared to an animal provided a diet that does notinclude the oligosaccharide composition. In some variations, the animalis poultry. In certain variations, the FCR of the poultry is reducedover 0 to 14 days of age, over 15 to 28 days of age, over 29 to 35 daysof age, over 35 days, over 42 days, over 6 weeks, over 6.5 weeks, over 0to 35 days of age, over 0 to 42 days of age, over 0 to 6 weeks of age,over 0 to 6.5 weeks of age, over 15 to 35 days of age, over 36 to 42days of age, over 15 to 39 days of age, or over 40 to 46 days of age.

In one embodiment, the FCR over 35 days for poultry provided anoligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is reduced by between 4 to 6% ascompared to poultry provided a diet that does not include theoligosaccharide composition. For example, in a certain embodiment, theFCR over 35 days for poultry provided an oligosaccharide composition,animal feed pre-mix, or animal feed composition as described herein is1.53, the FCR over 35 days for poultry provided a diet without theoligosaccharide composition is 1.61, and the FCR of the poultry providedthe oligosaccharide composition, animal feed pre-mix, or animal feedcomposition is reduced about 5% compared to the poultry provided a dietwithout the oligosaccharide composition. In some embodiments, the FCRover 42 days, over 6 weeks, or over 6.5 weeks days for poultry providedan oligosaccharide composition, animal feed pre-mix, or animal feedcomposition as described herein is reduced by between 4 to 6% ascompared to poultry provided a diet that does not include theoligosaccharide composition.

In some variations, an animal population provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein has a lower FCR compared to an animal populationprovided a diet that does not include the oligosaccharide composition,wherein the FCR is corrected for mortality in the animal population.

In certain variations, an animal provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition has a lowerFCR than an animal provided a diet that does not include theoligosaccharide composition, but which does include one or moreantibiotics, one or more ionophores, soluble corn fiber, modified wheatstarch, or yeast mannan, or any combinations thereof.

It is known to one skilled in the art, that when determining FCR, theFCR may be adjused for mortality to reduce noise due to small numberstatistics. Methods for adjusting FCR for mortality are well known toone skilled in the art.

In some embodiments that may be combined with any of the foregoingembodiments, the poultry is an individual poultry, while in otherembodiments the poultry is a poultry population.

In some variations, the animal is poultry, and the animal feedcomposition is poultry feed, wherein the oligosaccharide composition,poultry feed pre-mix, or poultry feed composition feed reduces feedconversion ratio (FCR) by up to about 10%, or about 5%, or between 1%and 10%, between 2% and 10%, between 3% and 10%, between 4% and 10%,between 5% and 10%, between 2% and 5%, between 2% and 6%, between 2% and7%, between 2% and 8%, between 2% and 9%, or between 1% and 5%, when fedto poultry as compared to poultry fed a feed composition without theoligosaccharide composition.

In certain variations, the poultry suffers from a disease or a disorder,or is raised in a challenged environment, wherein the oligosaccharidecomposition, poultry feed pre-mix, or poultry feed composition feedreduces feed conversion ratio (FCR) by up to about 30%, about 25%, about20%, about 15%, about 10%, or about 5%, or between 1% and 30%, between5% and 30%, between 10% and 30%, between 5% and 20%, between 10% and20%, between 1% and 20%, between 1% and 15%, between 1% and 10%, between2% and 10%, between 3% and 10%, between 4% and 10%, between 5% and 10%,between 2% and 5%, between 2% and 6%, between 2% and 7%, between 2% and8%, between 2% and 9%, or between 1% and 5%, when fed to poultry ascompared to poultry fed a feed composition without the oligosaccharidecomposition.

In some variations, the animal is swine, and the animal feed compositionis swine feed, wherein the oligosaccharide composition, swine feedpre-mix, or swine feed composition reduces feed conversion ratio (FCR)by up to about 15%, about 10%, or about 5%, or between 1% and 15%,between 2% and 15%, between 3% and 15%, between 4% and 15%, between 5%and 15%, between 10% and 15%, between 1% and 10%, between 2% and 10%,between 3% and 10%, between 4% and 10%, between 5% and 10%, between 2%and 5%, between 2% and 6%, between 2% and 7%, between 2% and 8%, between2% and 9%, or between 1% and 5%, when fed to swine as compared to swinefed a feed composition without the oligosaccharide composition.

In certain variations, the swine suffers from a disease or a disorder,or is raised in a challenged environment, wherein the oligosaccharidecomposition, swine feed pre-mix, or swine feed composition reduces feedconversion ratio (FCR) by up to about 40%, about 35% about 30%, about25%, about 20%, about 15%, about 10%, or about 5%, or between 1% and40%, between 5% and 40%, between 10% and 40%, between 15% and 40%,between 20% and 40%, between 25% and 40%, between 30% and 40%, between1% and 30%, between 5% and 30%, between 10% and 30%, between 5% and 20%,between 10% and 20%, between 1% and 20%, between 1% and 15%, between 1%and 10%, between 2% and 10%, between 3% and 10%, between 4% and 10%,between 5% and 10%, between 2% and 5%, between 2% and 6%, between 2% and7%, between 2% and 8%, between 2% and 9%, or between 1% and 5%, when fedto swine as compared to swine fed a feed composition without theoligosaccharide composition.

e) Mortality

In some variations, the mortality of an animal or animal populationprovided the oligosaccharide composition, animal feed pre-mix, or animalfeed composition as described herein may be reduced relative to themortality rate of an animal or animal population not provided theoligosaccharide composition, animal feed pre-mix, or animal feedcomposition. The reduction of mortality may include, for example, adecrease in the mortality rate on a per head basis. One of skill in theart would recognize that the mortality rate on a per head basis isdetermined as the ratio of the number of dead animals to the totalnumber of animals at the start of the performance period. The reductionin mortality may include, for example, a reduction in the mortality rateon a per weight basis. One skilled in the art would recognize that themortality rate on a per weight basis is determined as the ratio of thetotal weight of animals lost to mortality to the total weight of liveanimals plus the total weight of dead animals.

In some embodiments, the mortality rate on a per head basis for animalsprovided a base feed that does not include the oligosaccharidecomposition is at least 2%, at least 3%, at least 4%, at least 5%, atleast 10%, or at least 20%.

In some embodiments, providing the oligosaccharide composition, animalfeed pre-mix, or animal feed composition to an animal or animalpopulation results in a reduction in mortality rate on a per head basisof between 0 to 90%, between 0 to 80%, between 20 to 70%, between 30 to60%, between 40 to 60%, or between 45 to 55%, as compared to an animalor animal population that is not provided the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition.

For example, in one embodiment, a poultry population is provided ananimal feed composition as described herein and has a mortality rate of0.8% on a per head basis, compared to the mortality rate of 1.7% on aper head basis for a poultry population provided feed without anoligosaccharide composition. Thus, in one example, the mortality rate ona per head basis of a poultry population provided an animal feedcomposition is reduced 51% compared to a poultry population providedfeed without the oligosaccharide composition.

In certain variations, an animal provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition has a lowermortality rate than an animal provided a diet that does not include theoligosaccharide composition, but which does include one or moreantibiotics, one or more ionophores, soluble corn fiber, modified wheatstarch, or yeast mannan, or any combinations thereof.

f) Uniformity

In other embodiments, an animal population provided the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition has inimproved uniformity compared to an animal population that is notprovided the oligosaccharide composition, animal feed pre-mix, or animalfeed composition. Improving uniformity may include, for example,decreasing the relative variability of final body weight in a populationof animals, wherein the relative variability is the standard deviationof final body weight divided by the mean final body weight. In someembodiments, the relative variability in final body weight is reduced byat least 10%, at least 15%, at least 20%, at least 25%, at least 30%, atleast 35%, at least 40%, at least 45%, at least 50%, at least 55%, atleast 60%, at least 65%, at least 70%, between 10 to 75%, between 20 to60%, between 25 to 50%, between 25 to 40%, or between 30 to 40% for ananimal population provided the oligosaccharide composition, animal feedpre-mix, or animal feed composition has in improved uniformity comparedto an animal population that is not provided the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition.

In some variations, improving the uniformity of an animal population mayincrease the efficiency of animal processing, including, for example,mechanical processing to obtain meat from the animals.

In certain variations, an animal population provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition has greateruniformity than an animal population provided a diet that does notinclude the oligosaccharide composition, but which does include one ormore antibiotics, one or more ionophores, soluble corn fiber, modifiedwheat starch, or yeast mannan, or any combinations thereof.

In some embodiments that may be combined with any of the foregoingembodiments, the poultry is an individual poultry, while in otherembodiments the poultry is a poultry population.

g) Fatty Acid Concentration

In some embodiments, an animal that is fed the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition willexperience an increase in the volatile fatty acid (VFA) concentration inthe digestive system, compared to an animal not fed the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition. Volatilefatty acids may include, for example, acetic acid, butyric acid, orvaleric acid, or combinations thereof. In some embodiments, an animalthat is fed the oligosaccharide composition or the animal feedcomposition will experience an increase in the VFA concentration in thedigestive system, compared to the same animal before being fed theoligosaccharide composition or the animal feed composition. The VFAconcentration may be determined by any appropriate method known in theart (i.e. for example, gas chromatography). In certain embodiments, ananimal that is fed the oligosaccharide composition or the animal feedcomposition will experience an increase in VFA concentration in thedigestive system of about 1%, about 5%, about 8%, about 10%, about 15%,about 20%, about 25%, about 30%, about 40%, about 50%, about 60%, about70%, about 80%, about 90%, or about 100%.

In some embodiments, an animal that is fed the oligosaccharidecomposition, animal feed pre-mix, or the animal feed composition willexperience an increase in the short chain fatty acid (SCFA)concentration in the digestive system, compared to an animal not fed theoligosaccharide composition, animal feed pre-mix, or the animal feedcomposition. In some embodiments, an animal that is fed theoligosaccharide composition, animal feed pre-mix, or the animal feedcomposition will experience an increase in the SCFA concentration in thedigestive system, compared to the same animal before being fed theoligosaccharide composition, animal feed pre-mix, or the animal feedcomposition.

Short chain fatty acids include acetic, propionic, butyric, iso-butyric,2-methyl-butyric, valeric, iso-valeric, and lactic acid. The SCFAconcentration may be determined by any appropriate method known in theart (i.e. for example, gas chromatography). One of skill in the artwould appreciate that short chain fatty acids may exist and/or bedetermined as their respective conjugate bases (e.g., acetate,propionate, butyrate, iso-butyrate, 2-methyl-butyrate, valerate,iso-valerate, lactate).

In certain embodiments, an animal that is fed the oligosaccharidecomposition, animal feed pre-mix, or the animal feed composition willexperience an increase in SCFA concentration in the digestive system ofabout 1%, about 5%, about 8%, about 10%, about 15%, about 20%, about25%, about 30%, about 40%, about 50%, about 60%, about 70%, about 80%,about 90%, or about 100%.

In some embodiments, the animal will experience an increase in the ilealconcentration of SCFA. In other embodiments, the animal will experiencean increase in the cecal concentration of SCFA. In some variations, theanimal provided the oligosaccharide composition, animal feed pre-mix, oranimal feed composition as described herein will experience an increasein ileal concentration of SCFA or cecal concentration of SCFA, orcombination thereof, of at least 1%, at least 10%, at least 20%, atleast 30%, at least 40%, at least 50%, at least 60%, at least 70%,between 1 to 80%, between 10 to 80%, between 10 to 50%, between 30 to80%, or between 30 to 50% compared to an animal not provided theoligosaccharide composition, animal feed pre-mix, or animal feedcomposition. In certain variations, the SCFA is butyric acid, propionicacid, acetic acid, valeric acid, isobutyric acid, isovaleric acid,2-methyl-butyric acid, or lactic acid, or any combinations thereof. Inone variation, the SCFA is butyric acid or propionic acid, or acombination thereof.

In some embodiments, an animal that is fed the oligosaccharidecomposition will experience a reduction in the presence of pathogenic orotherwise harmful microorganisms within its digestive system. In someembodiments, the oligosaccharide composition provides a preferentialfood source for gut microorganisms that are natural competitors topathogenic or otherwise harmful microorganisms. In other embodiments,the oligosaccharide composition binds to the exterior surface (e.g.,exterior wall carbohydrate receptors) of pathogenic or otherwise harmfulmicroorganisms, suppressing their ability to colonize the gut, forexample by decreasing gut-adherence. In some embodiments, the pathogenicor otherwise harmful microorganisms are enterotoxigenic species orstrains. In certain embodiments, the pathogenic or otherwise harmfulmicroorganisms are selected from set including members of Campylobacterspp, Salmonella spp, and Eschericia spp. In one embodiment, thepathogenic or otherwise harmful microorganism is Campylobater jejuni orCampylobacter coli.

In some embodiments, an animal that is fed the oligosaccharidecomposition may not need to be provided antibiotics, or may require alower dose of antibiotics, in its diet. In some embodiment, an animalthat is fed the oligosaccharide composition but not fed antibiotics mayexhibit the same or better feed conversion ratio or feed efficiency thanan animal that is fed antibiotics but not the oligosaccharidecomposition.

In certain variations, an animal provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition has ahigher digestive system SCFA concentration, cecal SCFA concentration, orileal SCFA concentration than an animal provided a diet that does notinclude the oligosaccharide composition, but which does include one ormore antibiotics, one or more ionophores, soluble corn fiber, modifiedwheat starch, or yeast mannan, or any combinations thereof.

In some embodiments, an animal that is provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein may have greater access to nutrients in the diet thanan animal provided a diet that does not include the oligosaccharidecomposition. Nutrients to which an animal provided an oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein may have greater access may include, for example, aminoacids, metabolic energy, minerals, or vitamins, or any combinationsthereof. For example, in certain embodiments, a diet comprising theoligosaccharhide composition is more digestible to an animal than a dietthat does not comprise the oligosaccharide composition. Digestabilitymay be measured by, for example, comparing the amount of undigestednutrient residual in the excreta of the animal relative to the amount ofnutrient present in the feed.

In some embodiments that may be combined with any of the foregoingembodiments, the animal is poultry. In certain embodiments, the poultryis an individual poultry, while in other embodiments the poultry is apoultry population.

It should be understood that the methods described herein includeproviding to an animal or animal population any oligosaccharidecomposition, animal feed pre-mix, or animal feed composition asdescribed herein, to enhance the growth of the animal or animalpopulation in any way described herein. For example, provided herein isa method of enhancing growth of an animal population, comprising feedingto the animal population an animal feed,

-   -   wherein the animal feed comprises an oligosaccharide composition        at an inclusion rate of less than 5,000 ppm wt % dry        oligosaccharide composition per weight of animal feed;    -   wherein the oligosaccharide composition has a glycosidic bond        type distribution of:        -   at least 1 mol % α-(1,3) glycosidic linkages;        -   at least 1 mol % β-(1,3) glycosidic linkages; and        -   at least 15 mol % β-(1,6) glycosidic linkages, and    -   wherein at least 10 dry wt % of the oligosaccharide composition        has a degree of polymerization of at least 3; and    -   enhancing growth of the animal population.

In some embodiments that may be combined with any of the foregoingembodiments, enhancing the growth of the animal population may include,for example, an increase in weight gain, a decrease in the foodconversion ratio (FCR), an increase in digestibility of provided feed,an increase in released nutrients from provided feed, increase inaverage animal product yield, a reduced mortality rate, or an increasein animal uniformity, or any combinations thereof. The methods ofenhancing growth described herein may include providing an animal oranimal population with any oligosaccharide composition, animal feedpre-mix, or animal feed composition described herein.

In other embodiments that may be combined with any of the foregoingembodiments, the animal population may suffer from a disease ordisorder. For example, in certain embodiments, the disease or disorderis necrotic enteritis, coccidiosis, nutrient malabsorption syndrome,intestinal barrier breakdown, colisepticemia, yolk sack infection,salmonella infection, or campylobacter infection. In one embodiment, thedisease or disorder is necrotic enteritis. In some variations, theadministration of the oligosaccharide compositions, animal feedpre-mixes, or animal feed compositions described herein enhance thegrowth of the animal population suffering from such disease or disorder.

Methods of Providing the Oligosaccharide Composition to an Animal

The methods of enhancing growth of an animal or animal populationdescribed herein include providing an oligosaccharide composition,animal feed pre-mix, or animal feed to the animal or animal population.The oligosaccharide composition, animal feed pre-mix, or animal feed maybe provided in any suitable form, to any suitable type of animal, usingany suitable feeding schedule to enhance the growth of the animal oranimal population.

Type of Animal

The oligosaccharide composition, animal feed pre-mix, or the animal feedcomposition may be provided to any suitable animals. In someembodiments, the animal is monogastric. It is generally understood thata monogastric animal has a single-chambered stomach. In otherembodiments, the animal is a ruminant. It is generally understood that aruminant has a multi-chambered stomach. In some variations, the animalis a ruminant in the pre-ruminant phase. Examples of such ruminants inthe pre-ruminant phase include nursery calves.

In some variations, the animal is poultry. Examples of poultry includechicken, duck, turkey, goose, quail, or Cornish game hen. In onevariation, the animal is a chicken. In some embodiments, the poultry isa layer hen, a broiler chicken, or a turkey.

In other embodiments, the animal is a mammal, including, for example, acow, a pig, a goat, a sheep, a deer, a bison, a rabbit, an alpaca, allama, a mule, a horse, a reindeer, a water buffalo, a yak, a guineapig, a rat, a mouse, an alpaca, a dog, or a cat. In one variation, theanimal is a cow. In another variation, the animal is a pig.

The animal feed composition may also be used in aquaculture. In someembodiments, the animal is an aquatic animal. Examples of aquaticanimals may include a trout, a salmon, a bass, a tilapia, a shrimp, anoyster, a mussel, a clam, a lobster, or a crayfish. In one variation,the animal is a fish.

The oligosaccharide compositions described herein may be fed toindividual animals or an animal population. For example, in onevariation where the animal is poultry, the oligosaccharide compositionsmay be fed to an individual poultry or a poultry population.

Form of Animal Feed Composition

The oligosaccharide composition, animal feed pre-mix, or the animal feedcomposition may be provided to an animal in any appropriate form,including, for example, in solid form, in liquid form, or a combinationthereof. In certain embodiments, the oligosaccharide composition or theanimal feed composition is a liquid, such as a syrup or a solution. Inother embodiments, the oligosaccharide composition, animal feed pre-mix,or the animal feed composition is a solid, such as pellets or powder. Inyet other embodiments, the oligosaccharide composition, animal feedpre-mix, or the animal feed composition may be fed to the animal in bothliquid and solid components, such as in a mash.

Feeding Schedule

The oligosaccharide composition, animal feed pre-mix, or animal feedcomposition may be provided to the animal on any appropriate schedule.In some embodiments, the animal is provided the oligosaccharidecomposition, animal feed pre-mix, or animal feed composition on a dailybasis, on a weekly basis, on a monthly basis, on an every other daybasis, for at least three days out of every week, or for at least sevendays out of every month. In some embodiments, the animal is provided theoligosaccharide composition, animal feed pre-mix, or animal feedcomposition during certain diet phases.

For example, some animals are provided a starter diet between 0 to 14days of age. In other embodiments, an animal is provided a grower dietbetween 15 to 28 days of age, between 15 to 35 days of age, or beteen 15to 39 days of age. In still other embodiments, an animal is provided afinisher diet between 29 to 35 days of age, between 36 to 42 days ofage, or between 40 to 46 days of age.

In certain variations, the oligosaccharide composition, animal feedpre-mix, or animal feed composition is provided to the animal during thestarter diet phase, the grower diet phase, or the finisher diet phase,or any combinations thereof.

In certain embodiments, the animal is poultry, and the poultry isprovided a starter diet between 0 to 15 days of age, a grower dietbetween 16 to 28 days of age, and a finisher diet between 29 to 35 daysof age. In other embodiments, the animal is poultry, and the poultry isprovided a starter diet between 0 to 14 days of age, a grower dietbetween 15 to 35 days of age, and a finisher diet between 36 to 42 daysof age. In still other embodiments, the animal is poultry, and thepoultry is provided a starter diet between 0 to 14 days of age, a growerdiet between 15 to 39 days of age, and a finisher diet between 20 to 46days of age.

In some variations, the oligosaccharide composition, animal feedpre-mix, or animal feed composition is provided to the poultry duringthe starter diet phase, the grower diet phase, or the finisher dietphase, or any combinations thereof.

Methods of Producing Oligosaccharide Compositions

In one aspect, provided herein are methods of producing oligosaccharidecompositions suitable for use in an animal feed composition, an animalfeed pre-mix, or being fed directly to an animal. In some variations,the method includes combining feed sugar with a catalyst to form areaction mixture, and producing an oligosaccharide composition from atleast a portion of the reaction mixture. With reference to FIG. 1 ,process 100 depicts an exemplary process to produce an oligosaccharidecomposition from sugars, and such oligosaccharide composition producedcan subsequently be polished and further processed to form an animalfeed ingredient, such as an oligosaccharide syrup or powder. In step102, one or more sugars are combined with a catalyst in a reactor. Thesugars may include, for example, monosaccharides, disaccharides, and/ortrisaccharides. The catalyst has both acidic and ionic groups. In somevariations, the catalyst is a polymeric catalyst that includes acidicmonomers and ionic monomers. In other variations, the catalyst is asolid-supported catalyst that includes acidic moieties and ionicmoieties.

In step 104, the oligosaccharide composition in step 102 is polished toremove fine solids, reduce color, and reduce conductivity, and/or modifythe molecular weight distribution. Any suitable methods known in the artto polish the oligosaccharide composition may be used, including, forexample, the use of filtration units, carbon or other absorbents,chromatographic separators, or ion exchange columns. For example, in onevariation, the oligosaccharide composition is treated with powderedactivated carbon to reduce color, microfiltered to remove fine solids,and passed over a strong-acid cationic exchange resin and a weak-baseanionic exchange resin to remove salts. In another variation, theoligosaccharide composition is microfiltered to remove fine solids andpassed over a weak-base anionic exchange resin. In yet anothervariation, the oligosaccharide composition is passed through a simulatedmoving bed chromatographic separator to remove low molecular massspecies.

In step 106, the polished oligosaccharide composition undergoes furtherprocessing to produce either an oligosaccharide syrup or powder. Forexample, in one variation, the polished oligosaccharide is concentratedto form a syrup. Any suitable methods known in the art to concentrate asolution may be used, such as the use of a vacuum evaporator. In anothervariation, the polished oligosaccharide composition is spray dried toform a powder. Any suitable methods known in the art to spray dry asolution to form a powder may be used.

In other variations, process 100 may be modified to have additionalsteps. For example, the oligosaccharide composition produced in step 102may be diluted (e.g., in a dilution tank) and then undergo a carbontreatment to decolorize the oligosaccharide composition prior topolishing in step 104. In other variations, the oligosaccharidecomposition produced in step 102 may undergo further processing in asimulated moving bed (SMB) separation step to reduce digestiblecarbohydrate content.

In other variations, process 100 may be modified to have fewer steps.For example, in one variation, step 106 to produce the oligosaccharidesyrup or powder may be omitted, and the polished oligosaccharidecomposition of step 104 may be used directly as an ingredient to producean animal feed composition.

Each of the steps in exemplary process 100, the reactants and processingconditions in each step, as well as the compositions produced in eachstep are described in further detail below.

a) Feed Sugars

The feed sugar used in the methods of making oligosaccharidecompositions described herein may include one or more sugars. In someembodiments, the one or more sugars are selected from monosaccharides,disaccharides, trisaccharides, and short-chain oligosaccharides, or anymixtures thereof. In some embodiments, the one or more sugars aremonosaccharides, such as one or more C5 or C6 monosaccharides. Exemplarymonosaccharides include glucose, galactose, mannose, fructose, xylose,xylulose, and arabinose. In some embodiments, the one or more sugars areC5 monosaccharides. In other embodiments, the one or more sugars are C6monosaccharides. In some embodiments, the one or more sugars areselected from glucose, galactose, mannose, lactose, or theircorresponding sugar alcohols. In other embodiments, the one or moresugars are selected from fructose, xylose, arabinose, or theircorresponding sugar alcohols. In some embodiments, the one or moresugars are disaccharides. Exemplary disaccharides include lactose,sucrose and cellobiose. In some embodiments, the one or more sugars aretrisaccharides, such as maltotriose or raffinose. In some embodiments,the one or more sugars comprise a mixture of short-chainoligosaccharides, such as malto-dextrins. In certain embodiments, theone or more sugars are corn syrup obtained from the partial hydrolysisof corn starch. In a particular embodiment, the one or more sugars iscorn syrup with a dextrose equivalent (DE) below 50 (e.g., 10 DE cornsyrup, 18 DE corn syrup, 25 DE corn syrup, or 30 DE corn syrup).

In some embodiments, the method includes combining two or more sugarswith the catalyst to produce one or more oligosaccharides. In someembodiments, the two or more sugars are selected from glucose,galactose, mannose and lactose (e.g., glucose and galactose).

In other embodiments, the method includes combining a mixture of sugars(e.g., monosaccharides, disaccharides, trisaccharides, etc., and/orother short oligosaccharides) with the catalyst to produce one or moreoligosaccharides. In one embodiment, the method includes combining cornglucose syrup with the catalyst to produce one or more oligosaccharides.

In other embodiments, the method includes combining a polysaccharidewith the catalyst to produce one or more oligosaccharides. In someembodiments, the polysaccharide is selected from starch, guar gum,xanthan gum and acacia gum.

In other embodiments, the method includes combining a mixture of sugarsand sugar alcohols with the catalyst to produce one or moreoligosaccharides. In particular embodiments, the method includescombining one or more sugars and one or more alcohols selected from thegroup consisting of glucitol, sorbitol, xylitol and arabinatol, with thecatalyst to produce one or more oligosaccharides.

In certain variations, the feed sugar includes glucose, mannose,galactose, xylose, malto-dextrin, arabinose, or galactose, or anycombinations thereof. The choice of feed sugars will impact theresulting oligosaccharide composition produced. For example, in onevariation where the feed sugar is all glucose, the resultingoligosaccharide composition is a gluco-oligosaccharide. In anothervariation where the feed sugar is all mannose, the resultingoligosaccharide composition is a manno-oligosaccharide. In anothervariation wherein the feed sugar includes glucose and galactose, theresulting oligosaccharide composition is agluco-galacto-oligosaccharide. In yet another variation where the feedsugar is all xylose, the resulting oligosaccharide composition is axylo-oligosaccharide. In another variation where the feed sugar includesmalto-dextrin, the resulting oligosaccharide composition is agluco-oligosaccharide. In yet another variation where the feed sugarincludes xylose, glucose and galactose, the resulting oligosaccharidecomposition is a gluco-galacto-xylo-oligosaccharide. In one variationwhere the feed sugar includes arabinose and xylose, the resultingoligosaccharide composition is an arabino-xylo-oligosaccharide. Inanother variation where the feed sugar includes glucose and xylose, theresulting oligosaccharide composition is a gluco-xylo-oligosaccharide.In yet another variation where the feed sugar includes glucose,galactose and xylose, the resulting oligosaccharide composition is axylo-gluco-galacto-oligosaccharide.

In some variations to produce the oligosaccharide compositions herein,the sugars may be provided as a feed solution, in which the sugars arecombined with water and fed into the reactor. In other variations, thesugars may be fed into the reactor as a solid and combined with water inthe reactor.

The sugars used in the methods described herein may be obtained from anycommercially known sources, or produced according to any methods knownin the art.

b) Catalysts

The catalysts used in the methods of making oligosaccharide compositionsdescribed herein include polymeric catalysts and solid-supportedcatalysts.

In some embodiments, the catalyst is a polymer made up of acidicmonomers and ionic monomers (which are also referred to herein as“ionomers”) connected to form a polymeric backbone. Each acidic monomerincludes at least one Bronsted-Lowry acid, and each ionic monomerincludes at least one nitrogen-containing cationic group, at least onephosphorous-containing cationic group, or any combination thereof. Incertain embodiments of the polymeric catalyst, at least some of theacidic and ionic monomers may independently include a linker connectingthe Bronsted-Lowry acid or the cationic group (as applicable) to aportion of the polymeric backbone. For the acidic monomers, theBronsted-Lowry acid and the linker together form a side chain.Similarly, for the ionic monomers, the cationic group and the linkertogether form a side chain. With reference to the portion of thepolymeric catalyst depicted in FIGS. 2A and 2B, the side chains arependant from the polymeric backbone.

In another aspect, the catalyst is solid-supported, having acidicmoieties and ionic moieties each attached to a solid support. Eachacidic moiety independently includes at least one Bronsted-Lowry acid,and each ionic moiety includes at least one nitrogen-containing cationicgroup, at least one phosphorous-containing cationic group, or anycombination thereof. In certain embodiments of the solid-supportedcatalyst, at least some of the acidic and ionic moieties mayindependently include a linker connecting the Bronsted-Lowry acid or thecationic group (as applicable) to the solid support. With reference toFIG. 3 , the produced catalyst is a solid-supported catalyst with acidicand ionic moieties.

Acidic Monomers and Moieties

The polymeric catalysts include a plurality of acidic monomers, where asthe solid-supported catalysts include a plurality of acidic moietiesattached to a solid support.

In some embodiments, a plurality of acidic monomers (e.g., of apolymeric catalyst) or a plurality of acidic moieties (e.g., of asolid-supported catalyst) has at least one Bronsted-Lowry acid. Incertain embodiments, a plurality of acidic monomers (e.g., of apolymeric catalyst) or a plurality of acidic moieties (e.g., of asolid-supported catalyst) has one Bronsted-Lowry acid or twoBronsted-Lowry acids. In certain embodiments, a plurality of the acidicmonomers (e.g., of a polymeric catalyst) or a plurality of the acidicmoieties (e.g., of a solid-supported catalyst) has one Bronsted-Lowryacid, while others have two Bronsted-Lowry acids.

In some embodiments, each Bronsted-Lowry acid is independently selectedfrom sulfonic acid, phosphonic acid, acetic acid, isophthalic acid, andboronic acid. In certain embodiments, each Bronsted-Lowry acid isindependently sulfonic acid or phosphonic acid. In one embodiment, eachBronsted-Lowry acid is sulfonic acid. It should be understood that theBronsted-Lowry acids in an acidic monomer (e.g., of a polymericcatalyst) or an acidic moiety (e.g., of a solid-supported catalyst) maybe the same at each occurrence or different at one or more occurrences.

In some embodiments, one or more of the acidic monomers of a polymericcatalyst are directly connected to the polymeric backbone, or one ormore of the acidic moieties of a solid-supported catalyst are directlyconnected to the solid support. In other embodiments, one or more of theacidic monomers (e.g., of a polymeric catalyst) or one or more acidicmoieties (e.g., of a solid-supported catalyst) each independentlyfurther includes a linker connecting the Bronsted-Lowry acid to thepolymeric backbone or the solid support (as the case may be). In certainembodiments, some of the Bronsted-Lowry acids are directly connected tothe polymeric backbone or the solid support (as the case may be), whileother the Bronsted-Lowry acids are connected to the polymeric backboneor the solid support (as the case may be) by a linker.

In those embodiments where the Bronsted-Lowry acid is connected to thepolymeric backbone or the solid support (as the case may be) by alinker, each linker is independently selected from unsubstituted orsubstituted alkyl linker, unsubstituted or substituted cycloalkyllinker, unsubstituted or substituted alkenyl linker, unsubstituted orsubstituted aryl linker, and unsubstituted or substituted heteroaryllinker. In certain embodiments, the linker is unsubstituted orsubstituted aryl linker, or unsubstituted or substituted heteroaryllinker. In certain embodiments, the linker is unsubstituted orsubstituted aryl linker. In one embodiment, the linker is a phenyllinker. In another embodiment, the linker is a hydroxyl-substitutedphenyl linker.

In other embodiments, each linker in an acidic monomer (e.g., of apolymeric catalyst) or an acidic moiety (e.g., of a solid-supportedcatalyst) is independently selected from:

-   -   unsubstituted alkyl linker;    -   alkyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted cycloalkyl linker;    -   cycloalkyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted alkenyl linker;    -   alkenyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted aryl linker;    -   aryl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted heteroaryl linker; or    -   heteroaryl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino.

Further, it should be understood that some or all of the acidic monomers(e.g., of a polymeric catalyst) or one or more acidic moieties (e.g., ofa solid-supported catalyst) connected to the polymeric backbone by alinker may have the same linker, or independently have differentlinkers.

In some embodiments, each acidic monomer (e.g., of a polymeric catalyst)and each acidic moiety (e.g., of a solid-supported catalyst) mayindependently have the structure of Formulas IA-VIA:

wherein:

-   -   each Z is independently C(R²)(R³), N(R⁴), S, S(R⁵)(R⁶),        S(O)(R⁵)(R⁶), SO₂, or O, wherein any two adjacent Z can (to the        extent chemically feasible) be joined by a double bond, or taken        together to form cycloalkyl, heterocycloalkyl, aryl or        heteroaryl;    -   each m is independently selected from 0, 1, 2, and 3;    -   each n is independently selected from 0, 1, 2, and 3;    -   each R², R³, and R⁴ is independently hydrogen, alkyl,        heteroalkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl; and    -   each R⁵ and R⁶ is independently alkyl, heteroalkyl, cycloalkyl,        heterocyclyl, aryl, or heteroaryl.

In some embodiments, each acidic monomer (e.g., of a polymeric catalyst)and each acidic moiety (e.g., of a solid-supported catalyst) mayindependently have the structure of Formulas IA, IB, IVA, or IVB. Inother embodiments, each acidic monomer (e.g., of a polymeric catalyst)and each acidic moiety (e.g., of a solid-supported catalyst) mayindependently have the structure of Formulas IIA, IIB, IIC, IVA, IVB, orIVC. In other embodiments, each acidic monomer (e.g., of a polymericcatalyst) and each acidic moiety (e.g., of a solid-supported catalyst)may independently have the structure of Formulas IIIA, IIIB, or IIIC. Insome embodiments, each acidic monomer (e.g., of a polymeric catalyst)and each acidic moiety (e.g., of a solid-supported catalyst) mayindependently have the structure of Formulas VA, VB, or VC. In someembodiments, each acidic monomer (e.g., of a polymeric catalyst) andeach acidic moiety (e.g., of a solid-supported catalyst) mayindependently have the structure of Formula IA. In other embodiments,each acidic monomer (e.g., of a polymeric catalyst) and each acidicmoiety (e.g., of a solid-supported catalyst) may independently have thestructure of Formula IB.

In some embodiments, Z can be chosen from C(R₂)(R₃), N(R₄), SO₂, and O.In some embodiments, any two adjacent Z can be taken together to form agroup selected from a heterocycloalkyl, aryl, and heteroaryl. In otherembodiments, any two adjacent Z can be joined by a double bond. Anycombination of these embodiments is also contemplated (as chemicallyfeasible).

In some embodiments, m is 2 or 3. In other embodiments, n is 1, 2, or 3.In some embodiments, R¹ can be hydrogen, alkyl or heteroalkyl. In someembodiments, R¹ can be hydrogen, methyl, or ethyl. In some embodiments,each R², R³, and R⁴ can independently be hydrogen, alkyl, heterocyclyl,aryl, or heteroaryl. In other embodiments, each R², R³ and R⁴ canindependently be heteroalkyl, cycloalkyl, heterocyclyl, or heteroaryl.In some embodiments, each R⁵ and R⁶ can independently be alkyl,heterocyclyl, aryl, or heteroaryl. In another embodiment, any twoadjacent Z can be taken together to form cycloalkyl, heterocycloalkyl,aryl or heteroaryl.

In some embodiments, the polymeric catalysts and solid-supportedcatalysts described herein contain monomers or moieties, respectively,that have at least one Bronsted-Lowry acid and at least one cationicgroup. The Bronsted-Lowry acid and the cationic group can be ondifferent monomers/moieties or on the same monomer/moiety.

In certain embodiments, the acidic monomers of the polymeric catalystmay have a side chain with a Bronsted-Lowry acid that is connected tothe polymeric backbone by a linker. In certain embodiments, the acidicmoieties of the solid-supported catalyst may have a Bronsted-Lowry acidthat is attached to the solid support by a linker. Side chains (e.g., ofa polymeric catalyst) or acidic moieties (e.g., of a solid-supportedcatalyst) with one or more Bronsted-Lowry acids connected by a linkercan include, for example,

wherein:

-   -   L is an unsubstituted alkyl linker, alkyl linker substituted        with oxo, unsubstituted cycloalkyl, unsubstituted aryl,        unsubstituted heterocycloalkyl, and unsubstituted heteroaryl;        and    -   r is an integer.

In certain embodiments, L is an alkyl linker. In other embodiments L ismethyl, ethyl, propyl, or butyl. In yet other embodiments, the linker isethanoyl, propanoyl, or benzoyl. In certain embodiments, r is 1, 2, 3,4, or 5 (as applicable or chemically feasible).

In some embodiments, at least some of the acidic side chains (e.g., of apolymeric catalyst) and at least some of the acidic moieties (e.g., of asolid-supported catalyst) may be:

wherein:

-   -   s is 1 to 10;    -   each r is independently 1, 2, 3, 4, or 5 (as applicable or        chemically feasible); and    -   w is 0 to 10.

In certain embodiments, s is 1 to 9, or 1 to 8, or 1 to 7, or 1 to 6, or1 to 5, or 1 to 4, or 1 to 3, or 2, or 1. In certain embodiments, w is 0to 9, or 0 to 8, or 0 to 7, or 0 to 6, or 0 to 5, or 0 to 4, or 0 to 3,or 0 to 2, 1 or 0).

In certain embodiments, at least some of the acidic side chains (e.g.,of a polymeric catalyst) and at least some of the acidic moieties (e.g.,of a solid-supported catalyst) may be:

In other embodiments, the acidic monomers (e.g., of a polymericcatalyst) can have a side chain with a Bronsted-Lowry acid that isdirectly connected to the polymeric backbone. In other embodiments, theacidic moieties (e.g., of a solid-supported catalyst) may be directlyattached to a solid support. Side chains directly connect to thepolymeric backbone (e.g., of a polymeric catalyst) or acidic moieties(e.g., of a solid-supported catalyst) directly attached to the solidsupport may can include, for example,

Ionic Monomers and Moieties

The polymeric catalysts include a plurality of ionic monomers, where asthe solid-supported catalysts include a plurality of ionic moietiesattached to a solid support.

In some embodiments, a plurality of ionic monomers (e.g., of a polymericcatalyst) or a plurality of ionic moieties (e.g., of a solid-supportedcatalyst) has at least one nitrogen-containing cationic group, at leastone phosphorous-containing cationic group, or any combination thereof.In certain embodiments, a plurality of ionic monomers (e.g., of apolymeric catalyst) or a plurality of ionic moieties (e.g., of asolid-supported catalyst) has one nitrogen-containing cationic group orone phosphorous-containing cationic group. In some embodiments, aplurality of ionic monomers (e.g., of a polymeric catalyst) or aplurality of ionic moieties (e.g., of a solid-supported catalyst) hastwo nitrogen-containing cationic groups, two phosphorous-containingcationic group, or one nitrogen-containing cationic group and onephosphorous-containing cationic group. In other embodiments, a pluralityof ionic monomers (e.g., of a polymeric catalyst) or a plurality ofionic moieties (e.g., of a solid-supported catalyst) has onenitrogen-containing cationic group or phosphorous-containing cationicgroup, while others have two nitrogen-containing cationic groups orphosphorous-containing cationic groups.

In some embodiments, a plurality of ionic monomers (e.g., of a polymericcatalyst) or a plurality of ionic moieties (e.g., of a solid-supportedcatalyst) can have one cationic group, or two or more cationic groups,as is chemically feasible. When the ionic monomers (e.g., of a polymericcatalyst) or ionic moieties (e.g., of a solid-supported catalyst) havetwo or more cationic groups, the cationic groups can be the same ordifferent.

In some embodiments, each ionic monomer (e.g., of a polymeric catalyst)or each ionic moiety (e.g., of a solid-supported catalyst) is anitrogen-containing cationic group. In other embodiments, each ionicmonomer (e.g., of a polymeric catalyst) or each ionic moiety (e.g., of asolid-supported catalyst) is a phosphorous-containing cationic group. Inyet other embodiments, at least some of ionic monomers (e.g., of apolymeric catalyst) or at least some of the ionic moieties (e.g., of asolid-supported catalyst) are a nitrogen-containing cationic group,whereas the cationic groups in other ionic monomers (e.g., of apolymeric catalyst) or ionic moieties (e.g., of a solid-supportedcatalyst) are a phosphorous-containing cationic group. In an exemplaryembodiment, each cationic group in the polymeric catalyst orsolid-supported catalyst is imidazolium. In another exemplaryembodiment, the cationic group in some monomers (e.g., of a polymericcatalyst) or moieties (e.g., of a solid-supported catalyst) isimidazolium, while the cationic group in other monomers (e.g., of apolymeric catalyst) or moieties (e.g., of a solid-supported catalyst) ispyridinium. In yet another exemplary embodiment, each cationic group inthe polymeric catalyst or solid-supported catalyst is a substitutedphosphonium. In yet another exemplary embodiment, the cationic group insome monomers (e.g., of a polymeric catalyst) or moieties (e.g., of asolid-supported catalyst) is triphenyl phosphonium, while the cationicgroup in other monomers (e.g., of a polymeric catalyst) or moieties(e.g., of a solid-supported catalyst) is imidazolium.

In some embodiments, the nitrogen-containing cationic group at eachoccurrence can be independently selected from pyrrolium, imidazolium,pyrazolium, oxazolium, thiazolium, pyridinium, pyrimidinium, pyrazinium,pyridazinium, thiazinium, morpholinium, piperidinium, piperizinium, andpyrollizinium. In other embodiments, the nitrogen-containing cationicgroup at each occurrence can be independently selected from imidazolium,pyridinium, pyrimidinium, morpholinium, piperidinium, and piperizinium.In some embodiments, the nitrogen-containing cationic group can beimidazolium.

In some embodiments, the phosphorous-containing cationic group at eachoccurrence can be independently selected from triphenyl phosphonium,trimethyl phosphonium, triethyl phosphonium, tripropyl phosphonium,tributyl phosphonium, trichloro phosphonium, and trifluoro phosphonium.In other embodiments, the phosphorous-containing cationic group at eachoccurrence can be independently selected from triphenyl phosphonium,trimethyl phosphonium, and triethyl phosphonium. In other embodiments,the phosphorous-containing cationic group can be triphenyl phosphonium.

In some embodiments, one or more of the ionic monomers of a polymericcatalyst are directly connected to the polymeric backbone, or one ormore of the ionic moieties of a solid-supported catalyst are directlyconnected to the solid support. In other embodiments, one or more of theionic monomers (e.g., of a polymeric catalyst) or one or more ionicmoieties (e.g., of a solid-supported catalyst) each independentlyfurther includes a linker connecting the cationic group to the polymericbackbone or the solid support (as the case may be). In certainembodiments, some of the cationic groups are directly connected to thepolymeric backbone or the solid support (as the case may be), whileother the cationic groups are connected to the polymeric backbone or thesolid support (as the case may be) by a linker.

In those embodiments where the cationic group is connected to thepolymeric backbone or the solid support (as the case may be) by alinker, each linker is independently selected from unsubstituted orsubstituted alkyl linker, unsubstituted or substituted cycloalkyllinker, unsubstituted or substituted alkenyl linker, unsubstituted orsubstituted aryl linker, and unsubstituted or substituted heteroaryllinker. In certain embodiments, the linker is unsubstituted orsubstituted aryl linker, or unsubstituted or substituted heteroaryllinker. In certain embodiments, the linker is unsubstituted orsubstituted aryl linker. In one embodiment, the linker is a phenyllinker. In another embodiment, the linker is a hydroxyl-substitutedphenyl linker.

In other embodiments, each linker in an ionic monomer (e.g., of apolymeric catalyst) or an ionic moiety (e.g., of a solid-supportedcatalyst) is independently selected from:

-   -   unsubstituted alkyl linker;    -   alkyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted cycloalkyl linker;    -   cycloalkyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted alkenyl linker;    -   alkenyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted aryl linker;    -   aryl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted heteroaryl linker; or    -   heteroaryl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino.

Further, it should be understood that some or all of the ionic monomers(e.g., of a polymeric catalyst) or one or more ionic moieties (e.g., ofa solid-supported catalyst) connected to the polymeric backbone by alinker may have the same linker, or independently have differentlinkers.

In some embodiments, each ionic monomer (e.g., of a polymeric catalyst)or each ionic moiety (e.g., of a solid-supported catalyst) isindependently has the structure of Formulas VIIA-XIB:

wherein:

-   -   each Z is independently C(R²)(R³), N(R⁴), S, S(R⁵)(R⁶),        S(O)(R⁵)(R⁶), SO₂, or O, wherein any two adjacent Z can (to the        extent chemically feasible) be joined by a double bond, or taken        together to form cycloalkyl, heterocycloalkyl, aryl or        heteroaryl;    -   each X is independently F⁻, Cl⁻, Br⁻, I⁻, NO₂ ⁻, NO₃ ⁻, SO₄ ²⁻,        R⁷SO₂ ⁻, PO₄ ²⁻, R⁷PO₃, or R⁷PO₂ ⁻, where SO₄ ²⁻ and PO₄ ²⁻ are        each independently associated with at least two cationic groups        at any X position on any ionic monomer, and    -   each m is independently 0, 1, 2, or 3;    -   each n is independently 0, 1, 2, or 3;    -   each R¹, R², R³ and R⁴ is independently hydrogen, alkyl,        heteroalkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;    -   each R⁵ and R⁶ is independently alkyl, heteroalkyl, cycloalkyl,        heterocyclyl, aryl, or heteroaryl; and    -   each R⁷ is independently hydrogen, C₁₋₄alkyl, or C₁₋₄        heteroalkyl.

In some embodiments, Z can be chosen from C(R²)(R³), N(R⁴), SO₂, and O.In some embodiments, any two adjacent Z can be taken together to form agroup selected from a heterocycloalkyl, aryl and heteroaryl. In otherembodiments, any two adjacent Z can be joined by a double bond. In someembodiments, each X can be Cl⁻, NO₃ ⁻, SO₄ ²⁻, R⁷SO₄ ⁻, or R⁷CO₂ ⁻,where R⁷ can be hydrogen or C₁₋₄alkyl. In another embodiment, each X canbe Cl⁻, Br⁻, F, HSO₄ ⁻, HCO₂ ⁻, CH₃CO₂ ⁻, or NO₃ ⁻. In otherembodiments, X is acetate. In other embodiments, X is bisulfate. Inother embodiments, X is chloride. In other embodiments, X is nitrate.

In some embodiments, m is 2 or 3. In other embodiments, n is 1, 2, or 3.In some embodiments, each R², R³, and R⁴ can be independently hydrogen,alkyl, heterocyclyl, aryl, or heteroaryl. In other embodiments, each R²,R³ and R⁴ can be independently heteroalkyl, cycloalkyl, heterocyclyl, orheteroaryl. In some embodiments, each R⁵ and R⁶ can be independentlyalkyl, heterocyclyl, aryl, or heteroaryl. In another embodiment, any twoadjacent Z can be taken together to form cycloalkyl, heterocycloalkyl,aryl or heteroaryl.

In certain embodiments, the ionic monomers of the polymeric catalyst mayhave a side chain with a cationic group that is connected to thepolymeric backbone by a linker. In certain embodiments, the ionicmoieties of the solid-supported catalyst may have a cationic group thatis attached to the solid support by a linker. Side chains (e.g., of apolymeric catalyst) or ionic moieties (e.g., of a solid-supportedcatalyst) with one or more cationic groups connected by a linker caninclude, for example,

wherein:

-   -   L is an unsubstituted alkyl linker, alkyl linker substituted        with oxo, unsubstituted cycloalkyl, unsubstituted aryl,        unsubstituted heterocycloalkyl, and unsubstituted heteroaryl;    -   each R^(1a), R^(1b) and R^(1c) are independently hydrogen or        alkyl; or R^(1a) and R^(1b) are taken together with the nitrogen        atom to which they are attached to form an unsubstituted        heterocycloalkyl; or R^(1a) and R^(1b) are taken together with        the nitrogen atom to which they are attached to form an        unsubstituted heteroaryl or substituted heteroaryl, and R^(1c)        is absent;    -   r is an integer; and    -   X is as described above for Formulas VIIA-XIB.

In other embodiments L is methyl, ethyl, propyl, butyl. In yet otherembodiments, the linker is ethanoyl, propanoyl, benzoyl. In certainembodiments, r is 1, 2, 3, 4, or 5 (as applicable or chemicallyfeasible).

In other embodiments, each linker is independently selected from:

-   -   unsubstituted alkyl linker;    -   alkyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted cycloalkyl linker;    -   cycloalkyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted alkenyl linker;    -   alkenyl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted aryl linker;    -   aryl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino;    -   unsubstituted heteroaryl linker; or    -   heteroaryl linker substituted 1 to 5 substituents independently        selected from oxo, hydroxy, halo, amino.

In certain embodiments, each linker is an unsubstituted alkyl linker oran alkyl linker with an oxo substituent. In one embodiment, each linkeris —(CH₂)(CH₂)— or —(CH₂)(C═O). In certain embodiments, r is 1, 2, 3, 4,or 5 (as applicable or chemically feasible).

In some embodiments, at least some of the ionic side chains (e.g., of apolymeric catalyst) and at least some of the ionic moieties (e.g., of asolid-supported catalyst) may be:

wherein:

-   -   each R^(1a), R^(1b) and R^(1c) are independently hydrogen or        alkyl; or R^(1a) and R^(1b) are taken together with the nitrogen        atom to which they are attached to form an unsubstituted        heterocycloalkyl; or R^(1a) and R^(1b) are taken together with        the nitrogen atom to which they are attached to form an        unsubstituted heteroaryl or substituted heteroaryl, and R^(1c)        is absent;    -   s is an integer;    -   v is 0 to 10; and    -   X is as described above for Formulas VIIA-XIB.

In certain embodiments, s is 1 to 9, or 1 to 8, or 1 to 7, or 1 to 6, or1 to 5, or 1 to 4, or 1 to 3, or 2, or 1. In certain embodiments, v is 0to 9, or 0 to 8, or 0 to 7, or 0 to 6, or 0 to 5, or 0 to 4, or 0 to 3,or 0 to 2, 1 or 0).

In certain embodiments, at least some of the ionic side chains (e.g., ofa polymeric catalyst) and at least some of the ionic moieties (e.g., ofa solid-supported catalyst) may be:

In other embodiments, the ionic monomers (e.g., of a polymeric catalyst)can have a side chain with a cationic group that is directly connectedto the polymeric backbone. In other embodiments, the ionic moieties(e.g., of a solid-supported catalyst) can have a cationic group that isdirectly attached to the solid support. Side chains (e.g., of apolymeric catalyst) directly connect to the polymeric backbone or ionicmoieties (e.g., of a solid-supported catalyst) directly attached to thesolid support may can include, for example,

In some embodiments, the nitrogen-containing cationic group can be anN-oxide, where the negatively charged oxide (O—) is not readilydissociable from the nitrogen cation. Non-limiting examples of suchgroups include, for example,

In some embodiments, the phosphorous-containing side chain (e.g., of apolymeric catalyst) or moiety (e.g., of a solid-supported catalyst) isindependently:

In other embodiments, the ionic monomers (e.g., of a polymeric catalyst)can have a side chain with a cationic group that is directly connectedto the polymeric backbone. In other embodiments, the ionic moieties(e.g., of a solid-supported catalyst) can have a cationic group that isdirectly attached to the solid support. Side chains (e.g., of apolymeric catalyst) directly connect to the polymeric backbone or ionicmoieties (e.g., of a solid-supported catalyst) directly attached to thesolid support may can include, for example,

The ionic monomers (e.g., of a polymeric catalyst) or ionic moieties(e.g., of a solid-supported catalyst) can either all have the samecationic group, or can have different cationic groups. In someembodiments, each cationic group in the polymeric catalyst orsolid-supported catalyst is a nitrogen-containing cationic group. Inother embodiments, each cationic group in the polymeric catalyst orsolid-supported catalyst is a phosphorous-containing cationic group. Inyet other embodiments, the cationic group in some monomers or moietiesof the polymeric catalyst or solid-supported catalyst, respectively, isa nitrogen-containing cationic group, whereas the cationic group inother monomers or moieties of the polymeric catalyst or solid-supportedcatalyst, respectively, is a phosphorous-containing cationic group. Inan exemplary embodiment, each cationic group in the polymeric catalystor solid-supported catalyst is imidazolium. In another exemplaryembodiment, the cationic group in some monomers or moieties of thepolymeric catalyst or solid-supported catalyst is imidazolium, while thecationic group in other monomers or moieties of the polymeric catalystor solid-supported catalyst is pyridinium. In yet another exemplaryembodiment, each cationic group in the polymeric catalyst orsolid-supported catalyst is a substituted phosphonium. In yet anotherexemplary embodiment, the cationic group in some monomers or moieties ofthe polymeric catalyst or solid-supported catalyst is triphenylphosphonium, while the cationic group in other monomers or moieties ofthe polymeric catalyst or solid-supported catalyst is imidazolium.

Acidic-Ionic Monomers and Moieties

Some of the monomers in the polymeric catalyst contain both theBronsted-Lowry acid and the cationic group in the same monomer. Suchmonomers are referred to as “acidic-ionic monomers”. Similarly, some ofthe moieties in the solid-supported catalyst contain both theBronsted-Lowry acid and the cationic group in the same moieties. Suchmoieties are referred to as “acidic-ionic moieties”. For example, inexemplary embodiments, the acidic-ionic monomer (e.g., of a polymericcatalyst) or an acidic-ionic moiety (e.g., of a solid-supportedcatalyst) can contain imidazolium and acetic acid, or pyridinium andboronic acid.

In some embodiments, the monomers (e.g., of a polymeric catalyst) ormoieties (e.g., of a solid-supported catalyst) include bothBronsted-Lowry acid(s) and cationic group(s), where either theBronsted-Lowry acid is connected to the polymeric backbone (e.g., of apolymeric catalyst) or solid support (e.g., of a solid-supportedcatalyst) by a linker, and/or the cationic group is connected to thepolymeric backbone (e.g., of a polymeric catalyst) or is attached to thesolid support (e.g., of a solid-supported catalyst) by a linker.

It should be understood that any of the Bronsted-Lowry acids, cationicgroups and linkers (if present) suitable for the acidicmonomers/moieties and/or ionic monomers/moieties may be used in theacidic-ionic monomers/moieties.

In certain embodiments, the Bronsted-Lowry acid at each occurrence inthe acidic-ionic monomer (e.g., of a polymeric catalyst) or theacidic-ionic moiety (e.g., of a solid-supported catalyst) isindependently selected from sulfonic acid, phosphonic acid, acetic acid,isophthalic acid, and boronic acid. In certain embodiments, theBronsted-Lowry acid at each occurrence in the acidic-ionic monomer(e.g., of a polymeric catalyst) or the acidic-ionic moiety (e.g., of asolid-supported catalyst) is independently sulfonic acid or phosphonicacid. In one embodiment, the Bronsted-Lowry acid at each occurrence inthe acidic-ionic monomer (e.g., of a polymeric catalyst) or theacidic-ionic moiety (e.g., of a solid-supported catalyst) is sulfonicacid.

In some embodiments, the nitrogen-containing cationic group at eachoccurrence in the acidic-ionic monomer (e.g., of a polymeric catalyst)or the acidic-ionic moiety (e.g., of a solid-supported catalyst) isindependently selected from pyrrolium, imidazolium, pyrazolium,oxazolium, thiazolium, pyridinium, pyrimidinium, pyrazinium,pyridazinium, thiazinium, morpholinium, piperidinium, piperizinium, andpyrollizinium. In one embodiment, the nitrogen-containing cationic groupis imidazolium.

In some embodiments, the phosphorous-containing cationic group at eachoccurrence in the acidic-ionic monomer (e.g., of a polymeric catalyst)or the acidic-ionic moiety (e.g., of a solid-supported catalyst) isindependently selected from triphenyl phosphonium, trimethylphosphonium, triethyl phosphonium, tripropyl phosphonium, tributylphosphonium, trichloro phosphonium, and trifluoro phosphonium. In oneembodiment, the phosphorous-containing cationic group is triphenylphosphonium.

In some embodiments, the polymeric catalyst or solid-supported catalystcan include at least one acidic-ionic monomer or moiety, respectively,connected to the polymeric backbone or solid support, wherein at leastone acidic-ionic monomer or moiety includes at least one Bronsted-Lowryacid and at least one cationic group, and wherein at least one of theacidic-ionic monomers or moieties includes a linker connecting theacidic-ionic monomer to the polymeric backbone or solid support. Thecationic group can be a nitrogen-containing cationic group or aphosphorous-containing cationic group as described herein. The linkercan also be as described herein for either the acidic or ionic moieties.For example, the linker can be selected from unsubstituted orsubstituted alkyl linker, unsubstituted or substituted cycloalkyllinker, unsubstituted or substituted alkenyl linker, unsubstituted orsubstituted aryl linker, and unsubstituted or substituted heteroaryllinker.

In other embodiments, the monomers (e.g., of a polymeric catalyst) ormoieties (e.g., of a solid-supported catalyst) can have a side chaincontaining both a Bronsted-Lowry acid and a cationic group, where theBronsted-Lowry acid is directly connected to the polymeric backbone orsolid support, the cationic group is directly connected to the polymericbackbone or solid support, or both the Bronsted-Lowry acid and thecationic group are directly connected to the polymeric backbone or solidsupport.

In certain embodiments, the linker is unsubstituted or substituted aryllinker, or unsubstituted or substituted heteroaryl linker. In certainembodiments, the linker is unsubstituted or substituted aryl linker. Inone embodiment, the linker is a phenyl linker. In another embodiment,the linker is a hydroxyl-substituted phenyl linker.

Monomers of a polymeric catalyst that have side chains containing both aBronsted-Lowry acid and a cationic group can also be called “acidicionomers”. Acidic-ionic side chains (e.g., of a polymeric catalyst) oracidic-ionic moieties (e.g., of a solid-supported catalyst) that areconnected by a linker can include, for example,

wherein:

-   -   each X is independently selected from F⁻, Cl⁻, Br⁻, I⁻, NO₂ ⁻,        NO₃ ⁻, SO₄ ²⁻, R⁷SO₄ ⁻, R⁷CO₂ ⁻, PO₄ ²⁻, R⁷PO₃ ⁻, and R⁷PO₂,        where SO₄ ²⁻ and PO₄ ²⁻ are each independently associated with        at least two Bronsted-Lowry acids at any X position on any side        chain, and    -   each R⁷ is independently selected from hydrogen, C₁₋₄alkyl, and        C₁₋₄ heteroalkyl.

In some embodiments, R¹ can be selected from hydrogen, alkyl, andheteroalkyl. In some embodiments, R¹ can be selected from hydrogen,methyl, or ethyl. In some embodiments, each X can be selected from Cl⁻,NO₃ ⁻, SO₄ ²⁻, R⁷SO₄ ⁻, and R⁷CO₂ ⁻, where R⁷ can be selected fromhydrogen and C₁₋₄alkyl. In another embodiment, each X can be selectedfrom Cl⁻, Br⁻, I⁻, HSO₄ ⁻, HCO₂ ⁻, CH₃CO₂ ⁻, and NO₃ ⁻. In otherembodiments, X is acetate. In other embodiments, X is bisulfate. Inother embodiments, X is chloride. In other embodiments, X is nitrate.

In some embodiments, the acidic-ionic side chain (e.g., of a polymericcatalyst) or the acidic-ionic moiety (e.g., of a solid-supportedcatalyst) is independently:

In some embodiments, the acidic-ionic side chain (e.g., of a polymericcatalyst) or the acidic-ionic moiety (e.g., of a solid-supportedcatalyst) is independently:

In other embodiments, the monomers (e.g., of a polymeric catalyst) ormoieties (e.g., of a solid-supported catalyst) can have both aBronsted-Lowry acid and a cationic group, where the Bronsted-Lowry acidis directly connected to the polymeric backbone or solid support, thecationic group is directly connected to the polymeric backbone or solidsupport, or both the Bronsted-Lowry acid and the cationic group aredirectly connected to the polymeric backbone or solid support. Such sidechains in acidic-ionic monomers (e.g., of a polymeric catalyst) ormoieties (e.g., of a solid-supported catalyst) can include, for example,

Hydrophobic Monomers and Moieties

In some embodiments, the polymeric catalyst further includes hydrophobicmonomers connected to form the polymeric backbone. Similarly, in someembodiments, the solid-supported catalyst further includes hydrophobicmoieties attached to the solid support. In either instance, eachhydrophobic monomer or moiety has at least one hydrophobic group. Incertain embodiments of the polymeric catalyst or solid-supportedcatalyst, each hydrophobic monomer or moiety, respectively, has onehydrophobic group. In certain embodiments of the polymeric catalyst orsolid-supported catalyst, each hydrophobic monomer or moiety has twohydrophobic groups. In other embodiments of the polymeric catalyst orsolid-supported catalyst, some of the hydrophobic monomers or moietieshave one hydrophobic group, while others have two hydrophobic groups.

In some embodiments of the polymeric catalyst or solid-supportedcatalyst, each hydrophobic group is independently selected from anunsubstituted or substituted alkyl, an unsubstituted or substitutedcycloalkyl, an unsubstituted or substituted aryl, and an unsubstitutedor substituted heteroaryl. In certain embodiments of the polymericcatalyst or solid-supported catalyst, each hydrophobic group is anunsubstituted or substituted aryl, or an unsubstituted or substitutedheteroaryl. In one embodiment, each hydrophobic group is phenyl.Further, it should be understood that the hydrophobic monomers mayeither all have the same hydrophobic group, or may have differenthydrophobic groups.

In some embodiments of the polymeric catalyst, the hydrophobic group isdirectly connected to form the polymeric backbone. In some embodimentsof the solid-supported catalyst, the hydrophobic group is directlyattached to the solid support.

Other Characteristics of the Catalysts

In some embodiments, the acidic and ionic monomers make up a substantialportion of the polymeric catalyst. In some embodiments, the acidic andionic moieties make up a substantial portion solid-supported catalyst.In certain embodiments, the acidic and ionic monomers or moieties makeup at least about 30%, at least about 40%, at least about 50%, at leastabout 60%, at least about 70%, at least about 80%, at least about 90%,at least about 95%, or at least about 99% of the monomers or moieties ofthe catalyst, based on the ratio of the number of acidic and ionicmonomers/moieties to the total number of monomers/moieties present inthe catalyst.

In some embodiments, the polymeric catalyst or solid-supported catalysthas a total amount of Bronsted-Lowry acid of between about 0.1 and about20 mmol, between about 0.1 and about 15 mmol, between about 0.01 andabout 12 mmol, between about 0.05 and about 10 mmol, between about 1 andabout 8 mmol, between about 2 and about 7 mmol, between about 3 andabout 6 mmol, between about 1 and about 5, or between about 3 and about5 mmol per gram of the polymeric catalyst or solid-supported catalyst.

In some embodiments of the polymeric catalyst or solid-supportedcatalyst, each ionic monomer further includes a counterion for eachnitrogen-containing cationic group or phosphorous-containing cationicgroup. In certain embodiments of the polymeric catalyst orsolid-supported catalyst, each counterion is independently selected fromhalide, nitrate, sulfate, formate, acetate, or organosulfonate. In someembodiments of the polymeric catalyst or solid-supported catalyst, thecounterion is fluoride, chloride, bromide, or iodide. In one embodimentof the polymeric catalyst or solid-supported catalyst, the counterion ischloride. In another embodiment of the polymeric catalyst orsolid-supported catalyst, the counterion is sulfate. In yet anotherembodiment of the polymeric catalyst or solid-supported catalyst, thecounterion is acetate.

In some embodiments, the polymeric catalyst or solid-supported catalysthas a total amount of nitrogen-containing cationic groups andcounterions or a total amount of phosphorous-containing cationic groupsand counterions of between about 0.01 and about 10 mmol, between about0.05 and about 10 mmol, between about 1 and about 8 mmol, between about2 and about 6 mmol, or between about 3 and about 5 mmol per gram of thepolymeric catalyst or solid-supported catalyst.

In some embodiments, the acidic and ionic monomers make up a substantialportion of the polymeric catalyst or solid-supported catalyst. Incertain embodiments, the acidic and ionic monomers or moieties make upat least about 30%, at least about 40%, at least about 50%, at leastabout 60%, at least about 70%, at least about 80%, at least about 90%,at least about 95%, or at least about 99% of the monomers of thepolymeric catalyst or solid-supported catalyst, based on the ratio ofthe number of acidic and ionic monomers or moieties to the total numberof monomers or moieties present in the polymeric catalyst orsolid-supported catalyst.

The ratio of the total number of acidic monomers or moieties to thetotal number of ionic monomers or moieties can be varied to tune thestrength of the catalyst. In some embodiments, the total number ofacidic monomers or moieties exceeds the total number of ionic monomersor moieties in the polymer or solid support. In other embodiments, thetotal number of acidic monomers or moieties is at least about 2, atleast about 3, at least about 4, at least about 5, at least about 6, atleast about 7, at least about 8, at least about 9 or at least about 10times the total number of ionic monomers or moieties in the polymericcatalyst or solid-supported catalyst. In certain embodiments, the ratioof the total number of acidic monomers or moieties to the total numberof ionic monomers or moieties is about 1:1, about 2:1, about 3:1, about4:1, about 5:1, about 6:1, about 7:1, about 8:1, about 9:1 or about10:1.

In some embodiments, the total number of ionic monomers or moietiesexceeds the total number of acidic monomers or moieties in the catalyst.In other embodiments, the total number of ionic monomers or moieties isat least about 2, at least about 3, at least about 4, at least about 5,at least about 6, at least about 7, at least about 8, at least about 9or at least about 10 times the total number of acidic monomers ormoieties in the polymeric catalyst or solid-supported catalyst. Incertain embodiments, the ratio of the total number of ionic monomers ormoieties to the total number of acidic monomers or moieties is about1:1, about 2:1, about 3:1, about 4:1, about 5:1, about 6:1, about 7:1,about 8:1, about 9:1 or about 10:1.

Arrangement of Monomers in Polymeric Catalysts

In some embodiments of the polymeric catalysts, the acidic monomers, theionic monomers, the acidic-ionic monomers and the hydrophobic monomers,where present, can be arranged in alternating sequence or in a randomorder as blocks of monomers. In some embodiments, each block has notmore than twenty, fifteen, ten, six, or three monomers.

In some embodiments of the polymeric catalysts, the monomers of thepolymeric catalyst are randomly arranged in an alternating sequence.With reference to the portion of the polymeric catalyst depicted in FIG.9 , the monomers are randomly arranged in an alternating sequence.

In other embodiments of the polymeric catalysts, the monomers of thepolymeric catalyst are randomly arranged as blocks of monomers. Withreference to the portion of the polymeric catalyst depicted in FIG. 4 ,the monomers are arranged in blocks of monomers. In certain embodimentswhere the acidic monomers and the ionic monomers are arranged in blocksof monomers, each block has no more than 20, 19, 18, 17, 16, 15, 14, 13,12, 11, 10, 9, 8, 7, 6, 5, 4, or 3 monomers.

The polymeric catalysts described herein can also be cross-linked. Suchcross-linked polymeric catalysts can be prepared by introducingcross-linking groups. In some embodiments, cross-linking can occurwithin a given polymeric chain, with reference to the portion of thepolymeric catalysts depicted in FIGS. 5A and 5B. In other embodiments,cross-linking can occur between two or more polymeric chains, withreference to the portion of the polymeric catalysts in FIGS. 6A, 6B, 6Cand 6D.

With reference to FIGS. 5A, 5B and 6A, it should be understood that R¹,R² and R³, respectively, are exemplary cross linking groups. Suitablecross-linking groups that can be used to form a cross-linked polymericcatalyst with the polymers described herein include, for example,substituted or unsubstituted divinyl alkanes, substituted orunsubstituted divinyl cycloalkanes, substituted or unsubstituted divinylaryls, substituted or unsubstituted heteroaryls, dihaloalkanes,dihaloalkenes, and dihaloalkynes, where the substituents are those asdefined herein. For example, cross-linking groups can includedivinylbenzene, diallylbenzene, dichlorobenzene, divinylmethane,dichloromethane, divinylethane, dichloroethane, divinylpropane,dichloropropane, divinylbutane, dichlorobutane, ethylene glycol, andresorcinol. In one embodiment, the crosslinking group is divinylbenzene.

In some embodiments of the polymeric catalysts, the polymer iscross-linked. In certain embodiments, at least about 1%, at least about2%, at least about 3%, at least about 4%, at least about 5%, at leastabout 6%, at least about 7%, at least about 8%, at least about 9%, atleast about 10%, at least about 15%, at least about 20%, at least about30%, at least about 40%, at least about 50%, at least about 60%, atleast about 70%, at least about 80%, at least about 90% or at leastabout 99% of the polymer is cross-linked.

In some embodiments of the polymeric catalysts, the polymers describedherein are not substantially cross-linked, such as less than about 0.9%cross-linked, less than about 0.5% cross-linked, less than about 0.1%cross-linked, less than about 0.01% cross-linked, or less than 0.001%cross-linked.

Polymeric Backbones

In some embodiments, the polymeric backbone is formed from one or moresubstituted or unsubstituted monomers. Polymerization processes using awide variety of monomers are well known in the art (see, e.g.,International Union of Pure and Applied Chemistry, et al., IUPAC GoldBook, Polymerization. (2000)). One such process involves monomer(s) withunsaturated substitution, such as vinyl, propenyl, butenyl, or othersuch substitutent(s). These types of monomers can undergo radicalinitiation and chain polymerization.

In some embodiments, the polymeric backbone is formed from one or moresubstituted or unsubstituted monomers selected from ethylene, propylene,hydroxyethylene, acetaldehyde, styrene, divinyl benzene, isocyanates,vinyl chloride, vinyl phenols, tetrafluoroethylene, butylene,terephthalic acid, caprolactam, acrylonitrile, butadiene, ammonias,diammonias, pyrrole, imidazole, pyrazole, oxazole, thiazole, pyridine,pyrimidine, pyrazine, pyridazine, thiazine, morpholine, piperidine,piperizines, pyrollizine, triphenylphosphonate, trimethylphosphonate,triethylphosphonate, tripropylphosphonate, tributylphosphonate,trichlorophosphonate, trifluorophosphonate, and diazole.

The polymeric backbone of the polymeric catalysts described herein caninclude, for example, polyalkylenes, polyalkenyl alcohols,polycarbonates, polyarylenes, polyaryletherketones, andpolyamide-imides. In certain embodiments, the polymeric backbone can beselected from polyethylene, polypropylene, polyvinyl alcohol,polystyrene, polyurethane, polyvinyl chloride, polyphenol-aldehyde,polytetrafluoroethylene, polybutylene terephthalate, polycaprolactam,and poly(acrylonitrile butadiene styrene). In certain embodiments of thepolymeric catalyst, the polymeric backbone is polyethyelene orpolypropylene. In one embodiment of the polymeric catalyst, thepolymeric backbone is polyethylene. In another embodiment of thepolymeric catalyst, the polymeric backbone is polyvinyl alcohol. In yetanother embodiment of the polymeric catalyst, the polymeric backbone ispolystyrene.

With reference to FIG. 7 , in one embodiment, the polymeric backbone ispolyethylene. With reference to FIG. 8 , in another embodiment, thepolymeric backbone is polyvinyl alcohol.

The polymeric backbone described herein can also include an ionic groupintegrated as part of the polymeric backbone. Such polymeric backbonescan also be called “ionomeric backbones”. In certain embodiments, thepolymeric backbone can be selected from: polyalkyleneammonium,polyalkylenediammonium, polyalkylenepyrrolium, polyalkyleneimidazolium,polyalkylenepyrazolium, polyalkyleneoxazolium, polyalkylenethiazolium,polyalkylenepyridinium, polyalkylenepyrimidinium,polyalkylenepyrazinium, polyalkylenepyridazinium,polyalkylenethiazinium, polyalkylenemorpholinium,polyalkylenepiperidinium, polyalkylenepiperizinium,polyalkylenepyrollizinium, polyalkylenetriphenylphosphonium,polyalkylenetrimethylphosphonium, polyalkylenetriethylphosphonium,polyalkylenetripropylphosphonium, polyalkylenetributylphosphonium,polyalkylenetrichlorophosphonium, polyalkylenetrifluorophosphonium, andpolyalkylenediazolium, polyarylalkyleneammonium,polyarylalkylenediammonium, polyarylalkylenepyrrolium,polyarylalkyleneimidazolium, polyarylalkylenepyrazolium,polyarylalkyleneoxazolium, polyarylalkylenethiazolium,polyarylalkylenepyridinium, polyarylalkylenepyrimidinium,polyarylalkylenepyrazinium, polyarylalkylenepyridazinium,polyarylalkylenethiazinium, polyarylalkylenemorpholinium,polyarylalkylenepiperidinium, polyarylalkylenepiperizinium,polyarylalkylenepyrollizinium, polyarylalkylenetriphenylphosphonium,polyarylalkylenetrimethylphosphonium,polyarylalkylenetriethylphosphonium,polyarylalkylenetripropylphosphonium,polyarylalkylenetributylphosphonium,polyarylalkylenetrichlorophosphonium,polyarylalkylenetrifluorophosphonium, and polyarylalkylenediazolium.

Cationic polymeric backbones can be associated with one or more anions,including for example F⁻, Cl⁻, Br⁻, I⁻, NO₂ ⁻, NO₃ ⁻, SO₄ ²⁻, R⁷SO₄,R⁷CO₂, PO₄ ²⁻, R⁷PO₃ ⁻, and R⁷PO₂ ⁻, where R⁷ is selected from hydrogen,C₁₋₄alkyl, and C₁₋₄ heteroalkyl. In one embodiment, each anion can beselected from Cl⁻, Br⁻, I⁻, HSO₄ ⁻, HCO₂ ⁻, CH₃CO₂ ⁻, and NO₃ ⁻. Inother embodiments, each anion is acetate. In other embodiments, eachanion is bisulfate. In other embodiments, each anion is chloride. Inother embodiments, X is nitrate.

In other embodiments of the polymeric catalysts, the polymeric backboneis alkyleneimidazolium, which refers to an alkylene moiety, in which oneor more of the methylene units of the alkylene moiety has been replacedwith imidazolium. In one embodiment, the polymeric backbone is selectedfrom polyethyleneimidazolium, polyprolyeneimidazolium, andpolybutyleneimidazolium. It should further be understood that, in otherembodiments of the polymeric backbone, when a nitrogen-containingcationic group or a phosphorous-containing cationic group follows theterm “alkylene”, one or more of the methylene units of the alkylenemoiety is substituted with that nitrogen-containing cationic group orphosphorous-containing cationic group.

In other embodiments, monomers having heteroatoms can be combined withone or more difunctionalized compounds, such as dihaloalkanes,di(alkylsulfonyloxy)alkanes, and di(arylsulfonyloxy)alkanes to formpolymers. The monomers have at least two heteroatoms to link with thedifunctionalized alkane to create the polymeric chain. Thesedifunctionalized compounds can be further substituted as describedherein. In some embodiments, the difunctionalized compound(s) can beselected from 1,2-dichloroethane, 1,2-dichloropropane,1,3-dichloropropane, 1,2-dichlorobutane, 1,3-dichlorobutane,1,4-dichlorobutane, 1,2-dichloropentane, 1,3-dichloropentane,1,4-dichloropentane, 1,5-dichloropentane, 1,2-dibromoethane,1,2-dibromopropane, 1,3-dibromopropane, 1,2-dibromobutane,1,3-dibromobutane, 1,4-dibromobutane, 1,2-dibromopentane,1,3-dibromopentane, 1,4-dibromopentane, 1,5-dibromopentane,1,2-diiodoethane, 1,2-diiodopropane, 1,3-diiodopropane,1,2-diiodobutane, 1,3-diiodobutane, 1,4-diiodobutane, 1,2-diiodopentane,1,3-diiodopentane, 1,4-diiodopentane, 1,5-diiodopentane,1,2-dimethanesulfoxyethane, 1,2-dimethanesulfoxypropane,1,3-dimethanesulfoxypropane, 1,2-dimethanesulfoxybutane,1,3-dimethanesulfoxybutane, 1,4-dimethanesulfoxybutane,1,2-dimethanesulfoxypentane, 1,3-dimethanesulfoxypentane,1,4-dimethanesulfoxypentane, 1,5-dimethanesulfoxypentane,1,2-diethanesulfoxyethane, 1,2-diethanesulfoxypropane,1,3-diethanesulfoxypropane, 1,2-diethanesulfoxybutane,1,3-diethanesulfoxybutane, 1,4-diethanesulfoxybutane,1,2-diethanesulfoxypentane, 1,3-diethanesulfoxypentane,1,4-diethanesulfoxypentane, 1,5-diethanesulfoxypentane,1,2-dibenzenesulfoxyethane, 1,2-dibenzenesulfoxypropane,1,3-dibenzenesulfoxypropane, 1,2-dibenzenesulfoxybutane,1,3-dibenzenesulfoxybutane, 1,4-dibenzenesulfoxybutane,1,2-dibenzenesulfoxypentane, 1,3-dibenzenesulfoxypentane,1,4-dibenzenesulfoxypentane, 1,5-dibenzenesulfoxypentane,1,2-di-p-toluenesulfoxyethane, 1,2-di-p-toluenesulfoxypropane,1,3-di-p-toluenesulfoxypropane, 1,2-di-p-toluenesulfoxybutane,1,3-di-p-toluenesulfoxybutane, 1,4-di-p-toluenesulfoxybutane,1,2-di-p-toluenesulfoxypentane, 1,3-di-p-toluene sulfoxypentane,1,4-di-p-toluene sulfoxypentane, and 1,5-di-p-toluene sulfoxypentane.

Further, the number of atoms between side chains in the polymericbackbone can vary. In some embodiments, there are between zero andtwenty atoms, zero and ten atoms, zero and six atoms, or zero and threeatoms between side chains attached to the polymeric backbone.

In some embodiments, the polymer can be a homopolymer having at leasttwo monomer units, and where all the units contained within the polymerare derived from the same monomer in the same manner. In otherembodiments, the polymer can be a heteropolymer having at least twomonomer units, and where at least one monomeric unit contained withinthe polymer that differs from the other monomeric units in the polymer.The different monomer units in the polymer can be in a random order, inan alternating sequence of any length of a given monomer, or in blocksof monomers.

Other exemplary polymers include, for example, polyalkylene backbonesthat are substituted with one or more groups selected from hydroxyl,carboxylic acid, unsubstituted and substituted phenyl, halides,unsubstituted and substituted amines, unsubstituted and substitutedammonias, unsubstituted and substituted pyrroles, unsubstituted andsubstituted imidazoles, unsubstituted and substituted pyrazoles,unsubstituted and substituted oxazoles, unsubstituted and substitutedthiazoles, unsubstituted and substituted pyridines, unsubstituted andsubstituted pyrimidines, unsubstituted and substituted pyrazines,unsubstituted and substituted pyridazines, unsubstituted and substitutedthiazines, unsubstituted and substituted morpholines, unsubstituted andsubstituted piperidines, unsubstituted and substituted piperizines,unsubstituted and substituted pyrollizines, unsubstituted andsubstituted triphenylphosphonates, unsubstituted and substitutedtrimethylphosphonates, unsubstituted and substitutedtriethylphosphonates, unsubstituted and substitutedtripropylphosphonates, unsubstituted and substitutedtributylphosphonates, unsubstituted and substitutedtrichlorophosphonates, unsubstituted and substitutedtrifluorophosphonates, and unsubstituted and substituted diazoles.

For the polymers as described herein, multiple naming conventions arewell recognized in the art. For instance, a polyethylene backbone with adirect bond to an unsubstituted phenyl group(—CH₂—CH(phenyl)-CH₂—CH(phenyl)-) is also known as polystyrene. Shouldthat phenyl group be substituted with an ethenyl group, the polymer canbe named a polydivinylbenzene(—CH₂—CH(4-vinylphenyl)-CH₂—CH(4-vinylphenyl)-). Further examples ofheteropolymers may include those that are functionalized afterpolymerization.

One suitable example would be polystyrene-co-divinylbenzene:(—CH₂—CH(phenyl)-CH₂—CH(4-ethylenephenyl)-CH₂—CH(phenyl)-CH₂—CH(4-ethylenephenyl)-).Here, the ethenyl functionality could be at the 2, 3, or 4 position onthe phenyl ring.

With reference to FIG. 12 , in yet another embodiment, the polymericbackbone is a polyalkyleneimidazolium.

Further, the number of atoms between side chains in the polymericbackbone can vary. In some embodiments, there are between zero andtwenty atoms, zero and ten atoms, or zero and six atoms, or zero andthree atoms between side chains attached to the polymeric backbone. Withreference to FIG. 10 , in one embodiment, there are three carbon atomsbetween the side chain with the Bronsted-Lowry acid and the side chainwith the cationic group. In another example, with reference to FIG. 11 ,there are zero atoms between the side chain with the acidic moiety andthe side chain with the ionic moiety.

Solid Particles for Polymeric Catalysts

The polymeric catalysts described herein can form solid particles. Oneof skill in the art would recognize the various known techniques andmethods to make solid particles from the polymers described herein. Forexample, a solid particle can be formed through the procedures ofemulsion or dispersion polymerization, which are known to one of skillin the art. In other embodiments, the solid particles can be formed bygrinding or breaking the polymer into particles, which are alsotechniques and methods that are known to one of skill in the art.Methods known in the art to prepare solid particles include coating thepolymers described herein on the surface of a solid core. Suitablematerials for the solid core can include an inert material (e.g.,aluminum oxide, corn cob, crushed glass, chipped plastic, pumice,silicon carbide, or walnut shell) or a magnetic material. Polymericcoated core particles can be made by dispersion polymerization to grow across-linked polymer shell around the core material, or by spray coatingor melting.

Other methods known in the art to prepare solid particles includecoating the polymers described herein on the surface of a solid core.The solid core can be a non-catalytic support. Suitable materials forthe solid core can include an inert material (e.g., aluminum oxide, corncob, crushed glass, chipped plastic, pumice, silicon carbide, or walnutshell) or a magnetic material. In one embodiment of the polymericcatalyst, the solid core is made up of iron. Polymeric coated coreparticles can be made by techniques and methods that are known to one ofskill in the art, for example, by dispersion polymerization to grow across-linked polymer shell around the core material, or by spray coatingor melting.

The solid supported polymer catalyst particle can have a solid corewhere the polymer is coated on the surface of the solid core. In someembodiments, at least about 5%, at least about 10%, at least about 20%,at least about 30%, at least about 40%, or at least about 50% of thecatalytic activity of the solid particle can be present on or near theexterior surface of the solid particle. In some embodiments, the solidcore can have an inert material or a magnetic material. In oneembodiment, the solid core is made up of iron.

The solid particles coated with the polymer described herein have one ormore catalytic properties. In some embodiments, at least about 50%, atleast about 60%, at least about 70%, at least about 80% or at leastabout 90% of the catalytic activity of the solid particle is present onor near the exterior surface of the solid particle.

In some embodiments, the solid particle is substantially free of pores,for example, having no more than about 50%, no more than about 40%, nomore than about 30%, no more than about 20%, no more than about 15%, nomore than about 10%, no more than about 5%, or no more than about 1% ofpores. Porosity can be measured by methods well known in the art, suchas determining the Brunauer-Emmett-Teller (BET) surface area using theabsorption of nitrogen gas on the internal and external surfaces of amaterial (Brunauer, S. et al., J. Am. Chem. Soc. 1938, 60:309). Othermethods include measuring solvent retention by exposing the material toa suitable solvent (such as water), then removing it thermally tomeasure the volume of interior pores. Other solvents suitable forporosity measurement of the polymeric catalysts include, for example,polar solvents such as DMF, DMSO, acetone, and alcohols.

In other embodiments, the solid particles include a microporous gelresin. In yet other embodiments, the solid particles include amacroporous gel resin.

Support of the Solid-Supported Catalysts

In certain embodiments of the solid-supported catalyst, the support maybe selected from biochar, carbon, amorphous carbon, activated carbon,silica, silica gel, alumina, magnesia, titania, zirconia, clays (e.g.,kaolinite), magnesium silicate, silicon carbide, zeolites (e.g.,mordenite), ceramics, and any combinations thereof. In one embodiment,the support is carbon. The support for carbon support can be biochar,amorphous carbon, or activated carbon. In one embodiment, the support isactivated carbon.

The carbon support can have a surface area from 0.01 to 50 m²/g of drymaterial. The carbon support can have a density from 0.5 to 2.5 kg/L.The support can be characterized using any suitable instrumentalanalysis methods or techniques known in the art, including for examplescanning electron microscopy (SEM), powder X-ray diffraction (XRD),Raman spectroscopy, and Fourier Transform infrared spectroscopy (FTIR).The carbon support can be prepared from carbonaceous materials,including for example, shrimp shell, chitin, coconut shell, wood pulp,paper pulp, cotton, cellulose, hard wood, soft wood, wheat straw,sugarcane bagasse, cassava stem, corn stover, oil palm residue, bitumen,asphaltum, tar, coal, pitch, and any combinations thereof. One of skillin the art would recognize suitable methods to prepare the carbonsupports used herein. See e.g., M. Inagaki, L. R. Radovic, Carbon, vol.40, p. 2263 (2002), or A. G. Pandolfo and A. F. Hollenkamp, “Review:Carbon Properties and their role in supercapacitors,” Journal of PowerSources, vol. 157, pp. 11-27 (2006).

In other embodiments, the support is silica, silica gel, alumina, orsilica-alumina. One of skill in the art would recognize suitable methodsto prepare these silica- or alumina-based solid supports used herein.See e.g., Catalyst supports and supported catalysts, by A. B. Stiles,Butterworth Publishers, Stoneham Mass., 1987.

In yet other embodiments, the support is a combination of a carbonsupport, with one or more other supports selected from silica, silicagel, alumina, magnesia, titania, zirconia, clays (e.g., kaolinite),magnesium silicate, silicon carbide, zeolites (e.g., mordenite), andceramics.

Definitions

“Bronsted-Lowry acid” refers to a molecule, or substituent thereof, inneutral or ionic form that is capable of donating a proton (hydrogencation, H⁺).

“Homopolymer” refers to a polymer having at least two monomer units, andwhere all the units contained within the polymer are derived from thesame monomer. One suitable example is polyethylene, where ethylenemonomers are linked to form a uniform repeating chain (—CH₂—CH₂—CH₂—).Another suitable example is polyvinyl chloride, having a structure(—CH₂—CHCl—CH₂—CHCl—) where the —CH₂—CHCl— repeating unit is derivedfrom the H₂C═CHCl monomer.

“Heteropolymer” refers to a polymer having at least two monomer units,and where at least one monomeric unit differs from the other monomericunits in the polymer. Heteropolymer also refers to polymers havingdifunctionalized or trifunctionalized monomer units that can beincorporated in the polymer in different ways. The different monomerunits in the polymer can be in a random order, in an alternatingsequence of any length of a given monomer, or in blocks of monomers. Onesuitable example is polyethyleneimidazolium, where if in an alternatingsequence, would be the polymer depicted in FIG. 12 . Another suitableexample is polystyrene-co-divinylbenzene, where if in an alternatingsequence, could be(—CH₂—CH(phenyl)-CH₂—CH(4-ethylenephenyl)-CH₂—CH(phenyl)-CH₂—CH(4-ethylenephenyl)-).Here, the ethenyl functionality could be at the 2, 3, or 4 position onthe phenyl ring.

As used herein,

denotes the attachment point of a moiety to the parent structure.

When a range of values is listed, it is intended to encompass each valueand sub-range within the range. For example, “C₁₋₆ alkyl” (which mayalso be referred to as 1-6C alkyl, C1-C6 alkyl, or C1-6 alkyl) isintended to encompass, C₁, C₂, C₃, C₄, C₅, C₆, C₁₋₆, C₁₋₅, C₁₋₄, C₁₋₃,C₁₋₂, C₂₋₆, C₂₋₅, C₂₋₄, C₂₋₃, C₃₋₆, C₃₋₅, C₃₋₄, C₄₋₆, C₄₋₅, and C₅₋₆alkyl.

“Alkyl” includes saturated straight-chained or branched monovalenthydrocarbon radicals, which contain only C and H when unsubstituted. Insome embodiments, alkyl as used herein may have 1 to 10 carbon atoms(e.g., C₁₋₁₀ alkyl), 1 to 6 carbon atoms (e.g., C₁₋₆ alkyl), or 1 to 3carbon atoms (e.g., C₁₋₃ alkyl). Representative straight-chained alkylsinclude, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, andn-hexyl. Representative branched alkyls include, for example, isopropyl,sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl,3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, and2,3-dimethylbutyl. When an alkyl residue having a specific number ofcarbons is named, all geometric isomers having that number of carbonsare intended to be encompassed and described; thus, for example, “butyl”is meant to include n-butyl, sec-butyl, iso-butyl, and tert-butyl;“propyl” includes n-propyl, and iso-propyl.

“Alkoxy” refers to the group —O-alkyl, which is attached to the parentstructure through an oxygen atom. Examples of alkoxy may includemethoxy, ethoxy, propoxy, and isopropoxy. In some embodiments, alkoxy asused herein has 1 to 6 carbon atoms (e.g., O—(C₁₋₆ alkyl)), or 1 to 4carbon atoms (e.g., O—(C₁₋₄ alkyl)).

“Alkenyl” refers to straight-chained or branched monovalent hydrocarbonradicals, which contain only C and H when unsubstituted and at least onedouble bond. In some embodiments, alkenyl has 2 to 10 carbon atoms(e.g., C₂₋₁₀ alkenyl), or 2 to 5 carbon atoms (e.g., C₂₋₅ alkenyl). Whenan alkenyl residue having a specific number of carbons is named, allgeometric isomers having that number of carbons are intended to beencompassed and described; thus, for example, “butenyl” is meant toinclude n-butenyl, sec-butenyl, and iso-butenyl. Examples of alkenyl mayinclude —CH═CH₂, —CH₂—CH═CH₂ and —CH₂—CH═CH—CH═CH₂. The one or morecarbon-carbon double bonds can be internal (such as in 2-butenyl) orterminal (such as in 1-butenyl). Examples of C₂₋₄ alkenyl groups includeethenyl (C2), 1-propenyl (C3), 2-propenyl (C3), 1-butenyl (C4),2-butenyl (C4), and butadienyl (C4). Examples of C₂₋₆ alkenyl groupsinclude the aforementioned C₂₋₄ alkenyl groups as well as pentenyl (C5),pentadienyl (C5), and hexenyl (C6). Additional examples of alkenylinclude heptenyl (C7), octenyl (C8), and octatrienyl (C8).

“Alkynyl” refers to straight-chained or branched monovalent hydrocarbonradicals, which contain only C and H when unsubstituted and at least onetriple bond. In some embodiments, alkynyl has 2 to 10 carbon atoms(e.g., C₂₋₁₀ alkynyl), or 2 to 5 carbon atoms (e.g., C₂₋₅ alkynyl). Whenan alkynyl residue having a specific number of carbons is named, allgeometric isomers having that number of carbons are intended to beencompassed and described; thus, for example, “pentynyl” is meant toinclude n-pentynyl, sec-pentynyl, iso-pentynyl, and tert-pentynyl.Examples of alkynyl may include —C≡CH or —C≡C—CH₃.

In some embodiments, alkyl, alkoxy, alkenyl, and alkynyl at eachoccurrence may independently be unsubstituted or substituted by one ormore of substituents. In certain embodiments, substituted alkyl,substituted alkoxy, substituted alkenyl, and substituted alkynyl at eachoccurrence may independently have 1 to 5 substituents, 1 to 3substituents, 1 to 2 substituents, or 1 substituent. Examples of alkyl,alkoxy, alkenyl, and alkynyl substituents may include alkoxy,cycloalkyl, aryl, aryloxy, amino, amido, carbamate, carbonyl, oxo (═O),heteroalkyl (e.g., ether), heteroaryl, heterocycloalkyl, cyano, halo,haloalkoxy, haloalkyl, and thio. In certain embodiments, the one or moresubstituents of substituted alkyl, alkoxy, alkenyl, and alkynyl isindependently selected from cycloalkyl, aryl, heteroalkyl (e.g., ether),heteroaryl, heterocycloalkyl, cyano, halo, haloalkoxy, haloalkyl, oxo,—OR_(a), —N(R_(a))₂, —C(O)N(R_(a))₂, —N(R_(a))C(O)R_(a), —C(O)R_(a),—N(R_(a))S(O)_(t)R_(a) (where t is 1 or 2), —SR_(a), and—S(O)_(t)N(R_(a))₂ (where t is 1 or 2). In certain embodiments, eachR_(a) is independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl,heteroalkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl (e.g.,bonded through a ring carbon), —C(O)R′ and —S(O)_(t)R′ (where t is 1 or2), where each R′ is independently hydrogen, alkyl, alkenyl, alkynyl,haloalkyl, heteroalkyl, cycloalkyl, aryl, heterocycloalkyl, orheteroaryl. In one embodiment, R_(a) is independently hydrogen, alkyl,haloalkyl, cycloalkyl, aryl, aralkyl (e.g., alkyl substituted with aryl,bonded to parent structure through the alkyl group), heterocycloalkyl,or heteroaryl.

“Heteroalkyl”, “heteroalkenyl” and “heteroalkynyl” includes alkyl,alkenyl and alkynyl groups, respectively, wherein one or more skeletalchain atoms are selected from an atom other than carbon, e.g., oxygen,nitrogen, sulfur, phosphorus, or any combinations thereof. For example,heteroalkyl may be an ether where at least one of the carbon atoms inthe alkyl group is replaced with an oxygen atom. A numerical range canbe given, e.g., C₁₋₄ heteroalkyl which refers to the chain length intotal, which in this example is 4 atoms long. For example, a —CH₂OCH₂CH₃group is referred to as a “C₄” heteroalkyl, which includes theheteroatom center in the atom chain length description. Connection tothe rest of the parent structure can be through, in one embodiment, aheteroatom, or, in another embodiment, a carbon atom in the heteroalkylchain. Heteroalkyl groups may include, for example, ethers such asmethoxyethanyl (—CH₂CH₂OCH₃), ethoxymethanyl (—CH₂OCH₂CH₃),(methoxymethoxy)ethanyl (—CH₂CH₂OCH₂OCH₃), (methoxymethoxy)methanyl(—CH₂OCH₂OCH₃) and (methoxyethoxy)methanyl (—CH₂OCH₂ CH₂OCH₃); aminessuch as —CH₂CH₂NHCH₃, —CH₂CH₂N(CH₃)₂, —CH₂NHCH₂CH₃, and—CH₂N(CH₂CH₃)(CH₃). In some embodiments, heteroalkyl, heteroalkenyl, orheteroalkynyl may be unsubstituted or substituted by one or more ofsubstituents. In certain embodiments, a substituted heteroalkyl,heteroalkenyl, or heteroalkynyl may have 1 to 5 substituents, 1 to 3substituents, 1 to 2 substituents, or 1 substituent. Examples forheteroalkyl, heteroalkenyl, or heteroalkynyl substituents may includethe substituents described above for alkyl.

“Carbocyclyl” may include cycloalkyl, cycloalkenyl or cycloalkynyl.“Cycloalkyl” refers to a monocyclic or polycyclic alkyl group.“Cycloalkenyl” refers to a monocyclic or polycyclic alkenyl group (e.g.,containing at least one double bond). “Cycloalkynyl” refers to amonocyclic or polycyclic alkynyl group (e.g., containing at least onetriple bond). The cycloalkyl, cycloalkenyl, or cycloalkynyl can consistof one ring, such as cyclohexyl, or multiple rings, such as adamantyl. Acycloalkyl, cycloalkenyl, or cycloalkynyl with more than one ring can befused, spiro or bridged, or combinations thereof. In some embodiments,cycloalkyl, cycloalkenyl, and cycloalkynyl has 3 to 10 ring atoms (i.e.,C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, and C₃-C₁₀ cycloalkynyl), 3 to 8ring atoms (e.g., C₃-C₈ cycloalkyl, C₃-C₈ cycloalkenyl, and C₃-C₈cycloalkynyl), or 3 to 5 ring atoms (i.e., C₃-C₅ cycloalkyl, C₃-C₅cycloalkenyl, and C₃-C₅ cycloalkynyl). In certain embodiments,cycloalkyl, cycloalkenyl, or cycloalkynyl includes bridged andspiro-fused cyclic structures containing no heteroatoms. In otherembodiments, cycloalkyl, cycloalkenyl, or cycloalkynyl includesmonocyclic or fused-ring polycyclic (i.e., rings which share adjacentpairs of ring atoms) groups. C₃₋₆ carbocyclyl groups may include, forexample, cyclopropyl (C₃), cyclobutyl (C₄), cyclopentyl (C₅),cyclopentenyl (C₅), cyclohexyl (C₆), cyclohexenyl (C₆), andcyclohexadienyl (C₆). C₃₋₈ carbocyclyl groups may include, for example,the aforementioned C₃₋₆ carbocyclyl groups as well as cycloheptyl (C₇),cycloheptadienyl (C₇), cycloheptatrienyl (C₇), cyclooctyl (C₈),bicyclo[2.2.1]heptanyl, and bicyclo[2.2.2]octanyl. C₃₋₁₀ carbocyclylgroups may include, for example, the aforementioned C₃₋₈ carbocyclylgroups as well as octahydro-1H-indenyl, decahydronaphthalenyl, andspiro[4.5]decanyl.

“Heterocyclyl” refers to carbocyclyl as described above, with one ormore ring heteroatoms independently selected from nitrogen, oxygen,phosphorous, and sulfur. Heterocyclyl may include, for example,heterocycloalkyl, heterocycloalkenyl, and heterocycloalknyl. In someembodiments, heterocyclyl is a 3- to 18-membered non-aromatic monocyclicor polycyclic moiety that has at least one heteroatom selected fromnitrogen, oxygen, phosphorous and sulfur. In certain embodiments, theheterocyclyl can be a monocyclic or polycyclic (e.g., bicyclic,tricyclic or tetracyclic), wherein polycyclic ring systems can be afused, bridged or spiro ring system. Heterocyclyl polycyclic ringsystems can include one or more heteroatoms in one or both rings.

An N-containing heterocyclyl moiety refers to an non-aromatic group inwhich at least one of the skeletal atoms of the ring is a nitrogen atom.The heteroatom(s) in the heterocyclyl group is optionally oxidized. Oneor more nitrogen atoms, if present, are optionally quaternized. Incertain embodiments, heterocyclyl may also include ring systemssubstituted with one or more oxide (—O—) substituents, such aspiperidinyl N-oxides. The heterocyclyl is attached to the parentmolecular structure through any atom of the ring(s).

In some embodiments, heterocyclyl also includes ring systems with one ormore fused carbocyclyl, aryl or heteroaryl groups, wherein the point ofattachment is either on the carbocyclyl or heterocyclyl ring. In someembodiments, heterocyclyl is a 5-10 membered non-aromatic ring systemhaving ring carbon atoms and 1-4 ring heteroatoms, wherein eachheteroatom is independently selected from nitrogen, oxygen and sulfur(e.g., 5-10 membered heterocyclyl). In some embodiments, a heterocyclylgroup is a 5-8 membered non-aromatic ring system having ring carbonatoms and 1-4 ring heteroatoms, wherein each heteroatom is independentlyselected from nitrogen, oxygen and sulfur (e.g., 5-8 memberedheterocyclyl). In some embodiments, a heterocyclyl group is a 5-6membered non-aromatic ring system having ring carbon atoms and 1-4 ringheteroatoms, wherein each heteroatom is independently selected fromnitrogen, oxygen and sulfur (e.g., 5-6 membered heterocyclyl). In someembodiments, the 5-6 membered heterocyclyl has 1-3 ring heteroatomsselected from nitrogen, oxygen and sulfur. In some embodiments, the 5-6membered heterocyclyl has 1-2 ring heteroatoms selected from nitrogen,oxygen and sulfur. In some embodiments, the 5-6 membered heterocyclylhas 1 ring heteroatom selected from nitrogen, oxygen and sulfur.

“Aryl” refers to an aromatic group having a single ring (e.g., phenyl),multiple rings (e.g., biphenyl), or multiple fused rings (e.g.,naphthyl, fluorenyl, and anthryl). In some embodiments, aryl as usedherein has 6 to 10 ring atoms (e.g., C₆-C₁₀ aromatic or C₆-C₁₀ aryl)which has at least one ring having a conjugated pi electron system. Forexample, bivalent radicals formed from substituted benzene derivativesand having the free valences at ring atoms are named as substitutedphenylene radicals. In certain embodiments, aryl may have more than onering where at least one ring is non-aromatic can be connected to theparent structure at either an aromatic ring position or at anon-aromatic ring position. In certain embodiments, aryl includesmonocyclic or fused-ring polycyclic (i.e., rings which share adjacentpairs of ring atoms) groups.

“Heteroaryl” refers to an aromatic group having a single ring, multiplerings, or multiple fused rings, with one or more ring heteroatomsindependently selected from nitrogen, oxygen, phosphorous, and sulfur.In some embodiments, heteroaryl is an aromatic, monocyclic or bicyclicring containing one or more heteroatoms independently selected fromnitrogen, oxygen and sulfur with the remaining ring atoms being carbon.In certain embodiments, heteroaryl is a 5- to 18-membered monocyclic orpolycyclic (e.g., bicyclic or tricyclic) aromatic ring system (e.g.,having 6, 10 or 14 pi electrons shared in a cyclic array) having ringcarbon atoms and 1 to 6 ring heteroatoms provided in the aromatic ringsystem, wherein each heteroatom is independently selected from nitrogen,oxygen, phosphorous and sulfur (e.g., 5-18 membered heteroaryl). Incertain embodiments, heteroaryl may have a single ring (e.g., pyridyl,pyridinyl, imidazolyl) or multiple condensed rings (e.g., indolizinyl,benzothienyl) which condensed rings may or may not be aromatic. In otherembodiments, heteroaryl may have more than one ring where at least onering is non-aromatic can be connected to the parent structure at eitheran aromatic ring position or at a non-aromatic ring position. In oneembodiment, heteroaryl may have more than one ring where at least onering is non-aromatic is connected to the parent structure at an aromaticring position. Heteroaryl polycyclic ring systems can include one ormore heteroatoms in one or both rings.

For example, in one embodiment, an N-containing “heteroaryl” refers toan aromatic group in which at least one of the skeletal atoms of thering is a nitrogen atom. One or more heteroatom(s) in the heteroarylgroup can be optionally oxidized. One or more nitrogen atoms, ifpresent, are optionally quaternized. In other embodiments, heteroarylmay include ring systems substituted with one or more oxide (—O—)substituents, such as pyridinyl N-oxides. The heteroaryl may be attachedto the parent molecular structure through any atom of the ring(s).

In other embodiments, heteroaryl may include ring systems with one ormore fused aryl groups, wherein the point of attachment is either on thearyl or on the heteroaryl ring. In yet other embodiments, heteroaryl mayinclude ring systems with one or more carbocyclyl or heterocyclyl groupswherein the point of attachment is on the heteroaryl ring. Forpolycyclic heteroaryl groups wherein one ring does not contain aheteroatom (e.g., indolyl, quinolinyl, and carbazolyl) the point ofattachment can be on either ring, i.e., either the ring bearing aheteroatom (e.g., 2-indolyl) or the ring that does not contain aheteroatom (e.g., 5-indolyl). In some embodiments, a heteroaryl group isa 5-10 membered aromatic ring system having ring carbon atoms and 1-4ring heteroatoms provided in the aromatic ring system, wherein eachheteroatom is independently selected from nitrogen, oxygen, phosphorous,and sulfur (e.g., 5-10 membered heteroaryl). In some embodiments, aheteroaryl group is a 5-8 membered aromatic ring system having ringcarbon atoms and 1-4 ring heteroatoms provided in the aromatic ringsystem, wherein each heteroatom is independently selected from nitrogen,oxygen, phosphorous, and sulfur (e.g., 5-8 membered heteroaryl). In someembodiments, a heteroaryl group is a 5-6 membered aromatic ring systemhaving ring carbon atoms and 1-4 ring heteroatoms provided in thearomatic ring system, wherein each heteroatom is independently selectedfrom nitrogen, oxygen, phosphorous, and sulfur (e.g., 5-6 memberedheteroaryl). In some embodiments, the 5-6 membered heteroaryl has 1-3ring heteroatoms selected from nitrogen, oxygen, phosphorous, andsulfur. In some embodiments, the 5-6 membered heteroaryl has 1-2 ringheteroatoms selected from nitrogen, oxygen, phosphorous, and sulfur. Insome embodiments, the 5-6 membered heteroaryl has 1 ring heteroatomselected from nitrogen, oxygen, phosphorous, and sulfur.

In some embodiments, carbocyclyl (including, for example, cycloalkyl,cycloalkenyl or cycloalkynyl), aryl, heteroaryl, and heterocyclyl ateach occurrence may independently be unsubstituted or substituted by oneor more of substituents. In certain embodiments, a substitutedcarbocyclyl (including, for example, substituted cycloalkyl, substitutedcycloalkenyl or substituted cycloalkynyl), substituted aryl, substitutedheteroaryl, substituted heterocyclyl at each occurrence may beindependently may independently have 1 to 5 substituents, 1 to 3substituents, 1 to 2 substituents, or 1 substituent. Examples ofcarbocyclyl (including, for example, cycloalkyl, cycloalkenyl orcycloalkynyl), aryl, heteroaryl, heterocyclyl substituents may includealkyl alkenyl, alkoxy, cycloalkyl, aryl, heteroalkyl (e.g., ether),heteroaryl, heterocycloalkyl, cyano, halo, haloalkoxy, haloalkyl, oxo(═O), —OR_(a), —N(R_(a))₂, —C(O)N(R_(a))₂, —N(R_(a))C(O)R_(a),—C(O)R_(a), —N(R_(a))S(O)_(t)R_(a) (where t is 1 or 2), —SR_(a), and—S(O)_(t)N(R_(a))₂ (where t is 1 or 2), wherein R_(a) is as describedherein.

It should be understood that, as used herein, any moiety referred to asa “linker” refers to the moiety has having bivalency. Thus, for example,“alkyl linker” refers to the same residues as alkyl, but havingbivalency. Examples of alkyl linkers include —CH₂—, —CH₂CH₂—,—CH₂CH₂CH₂—, and —CH₂CH₂CH₂CH₂—. “Alkenyl linker” refers to the sameresidues as alkenyl, but having bivalency. Examples of alkenyl linkersinclude —CH═CH—, —CH₂—CH═CH— and —CH₂—CH═CH—CH₂—. “Alkynyl linker”refers to the same residues as alkynyl, but having bivalency. Examplesalkynyl linkers include —C≡C— or —C≡C—CH₂—. Similarly, “carbocyclyllinker”, “aryl linker”, “heteroaryl linker”, and “heterocyclyl linker”refer to the same residues as carbocyclyl, aryl, heteroaryl, andheterocyclyl, respectively, but having bivalency.

“Amino” or “amine” refers to —N(R_(a))(R_(b)), where each R_(a) andR_(b) is independently selected from hydrogen, alkyl, alkenyl, alkynyl,haloalkyl, heteroalkyl (e.g., bonded through a chain carbon),cycloalkyl, aryl, heterocycloalkyl (e.g., bonded through a ring carbon),heteroaryl (e.g., bonded through a ring carbon), —C(O)R′ and —S(O)_(t)R′(where t is 1 or 2), where each R′ is independently hydrogen, alkyl,alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, aryl,heterocycloalkyl, or heteroaryl. It should be understood that, in oneembodiment, amino includes amido (e.g., —NR_(a)C(O)R_(b)). It should befurther understood that in certain embodiments, the alkyl, alkenyl,alkynyl, haloalkyl, heteroalkyl, cycloalkyl, aryl, heterocycloalkyl, orheteroaryl moiety of R_(a) and R_(b) may be further substituted asdescribed herein. R_(a) and R_(b) may be the same or different. Forexample, in one embodiment, amino is —NH₂ (where R_(a) and R_(b) areeach hydrogen). In other embodiments where R_(a) and R_(b) are otherthan hydrogen, R_(a) and R_(b) can be combined with the nitrogen atom towhich they are attached to form a 3-, 4-, 5-, 6-, or 7-membered ring.Such examples may include 1-pyrrolidinyl and 4-morpholinyl.

“Ammonium” refers to —N(R_(a))(R_(b))(R_(c))⁺, where each R_(a), R_(b)and R_(c) is independently selected from hydrogen, alkyl, alkenyl,alkynyl, haloalkyl, heteroalkyl (e.g., bonded through a chain carbon),cycloalkyl, aryl, heterocycloalkyl (e.g., bonded through a ring carbon),heteroaryl (e.g., bonded through a ring carbon), —C(O)R′ and —S(O)_(t)R′(where t is 1 or 2), where each R′ is independently hydrogen, alkyl,alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, aryl,heterocycloalkyl, or heteroaryl; or any two of R_(a), R_(b) and R_(c)may be taken together with the atom to which they are attached to form acycloalkyl, heterocycloalkyl; or any three of R_(a), R_(b) and R_(c) maybe taken together with the atom to which they are attached to form arylor heteroaryl. It should be further understood that in certainembodiments, the alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl,cycloalkyl, aryl, heterocycloalkyl, or heteroaryl moiety of any one ormore of R_(a), R_(b) and R_(c) may be further substituted as describedherein. R_(a), R_(b) and R_(c) may be the same or different.

In certain embodiments, “amino” also refers to N-oxides of the groups—N⁺(H)(R_(a))O⁻, and —N⁺(R_(a))(R_(b))O—, where R_(a) and R_(b) are asdescribed herein, where the N-oxide is bonded to the parent structurethrough the N atom. N-oxides can be prepared by treatment of thecorresponding amino group with, for example, hydrogen peroxide orm-chloroperoxybenzoic acid. The person skilled in the art is familiarwith reaction conditions for carrying out the N-oxidation.

“Amide” or “amido” refers to a chemical moiety with formula —C(O)N(R_(a))(R_(b)) or —NR^(a)C(O)R_(b), where R_(a) and R_(b) at eachoccurrence are as described herein. In some embodiments, amido is a C₁₋₄amido, which includes the amide carbonyl in the total number of carbonsin the group. When a —C(O) N(R_(a))(R_(b)) has R_(a) and R_(b) otherthan hydrogen, they can be combined with the nitrogen atom to form a 3-,4-, 5-, 6-, or 7-membered ring.

“Carbonyl” refers to —C(O)R_(a), where R_(a) is hydrogen, alkyl,alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, aryl,heterocycloalkyl, heteroaryl, —N(R′)₂, —S(O)_(t)R′, where each R′ isindependently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl,cycloalkyl, aryl, heterocycloalkyl, or heteroaryl, and t is 1 or 2. Incertain embodiments where each R′ are other than hydrogen, the two R′moieties can be combined with the nitrogen atom to which they areattached to form a 3-, 4-, 5-, 6-, or 7-membered ring. It should beunderstood that, in one embodiment, carbonyl includes amido (e.g., —C(O)N(R_(a))(R_(b))).

“Carbamate” refers to any of the following groups:—O—C(═O)—N(R_(a))(R_(b)) and —N(R_(a))—C(═O)—OR_(b), wherein R_(a) andR_(b) at each occurrence are as described herein.

“Cyano” refers to a —CN group.

“Halo”, “halide”, or, alternatively, “halogen” means fluoro, chloro,bromo or iodo. The terms “haloalkyl,” “haloalkenyl,” “haloalkynyl” and“haloalkoxy” include alkyl, alkenyl, alkynyl and alkoxy moieties asdescribed above, wherein one or more hydrogen atoms are replaced byhalo. For example, where a residue is substituted with more than onehalo groups, it may be referred to by using a prefix corresponding tothe number of halo groups attached. For example, dihaloaryl,dihaloalkyl, and trihaloaryl refer to aryl and alkyl substituted withtwo (“di”) or three (“tri”) halo groups, which may be, but are notnecessarily, the same halogen; thus, for example, 3,5-difluorophenyl,3-chloro-5-fluorophenyl, 4-chloro-3-fluorophenyl, and3,5-difluoro-4-chlorophenyl is within the scope of dihaloaryl. Otherexamples of a haloalkyl group include difluoromethyl (—CHF₂),trifluoromethyl (—CF₃), 2,2,2-trifluoroethyl, and1-fluoromethyl-2-fluoroethyl. Each of the alkyl, alkenyl, alkynyl andalkoxy groups of haloalkyl, haloalkenyl, haloalkynyl and haloalkoxy,respectively, can be optionally substituted as defined herein.“Perhaloalkyl” refers to an alkyl or alkylene group in which all of thehydrogen atoms have been replaced with a halogen (e.g., fluoro, chloro,bromo, or iodo). In some embodiments, all of the hydrogen atoms are eachreplaced with fluoro. In some embodiments, all of the hydrogen atoms areeach replaced with chloro. Examples of perhaloalkyl groups include —CF₃,—CF₂CF₃, —CF₂CF₂CF₃, —CCl₃, —CFCl₂, and —CF₂Cl.

“Thio” refers to —SR_(a), wherein R_(a) is as described herein. “Thiol”refers to the group —R_(a)SH, wherein R_(a) is as described herein.

“Sulfinyl” refers to —S(O)R_(a). In some embodiments, sulfinyl is—S(O)N(R_(a))(R_(b)). “Sulfonyl” refers to the —S(O₂)R_(a). In someembodiments, sulfonyl is —S(O₂) N(R_(a))(R_(b)) or —S(O₂)OH. For each ofthese moieties, it should be understood that R_(a) and R_(b) are asdescribed herein.

“Moiety” refers to a specific segment or functional group of a molecule.Chemical moieties are often recognized chemical entities embedded in orappended to a molecule.

As used herein, the term “unsubstituted” means that for carbon atoms,only hydrogen atoms are present besides those valencies linking the atomto the parent molecular group. One example is propyl (—CH₂—CH₂—CH₃). Fornitrogen atoms, valencies not linking the atom to the parent moleculargroup are either hydrogen or an electron pair. For sulfur atoms,valencies not linking the atom to the parent molecular group are eitherhydrogen, oxygen or electron pair(s).

As used herein, the term “substituted” or “substitution” means that atleast one hydrogen present on a group (e.g., a carbon or nitrogen atom)is replaced with a permissible substituent, e.g., a substituent whichupon substitution for the hydrogen results in a stable compound, e.g., acompound which does not spontaneously undergo transformation such as byrearrangement, cyclization, elimination, or other reaction. Unlessotherwise indicated, a “substituted” group can have a substituent at oneor more substitutable positions of the group, and when more than oneposition in any given structure is substituted, the substituent iseither the same or different at each position. Substituents include oneor more group(s) individually and independently selected from alkylalkenyl, alkoxy, cycloalkyl, aryl, heteroalkyl (e.g., ether),heteroaryl, heterocycloalkyl, cyano, halo, haloalkoxy, haloalkyl, oxo(═O), —OR_(a), —N(R_(a))₂, —C(O)N(R_(a))₂, —N(R_(a))C(O)R_(a),—C(O)R_(a), —N(R_(a))S(O)_(t)R_(a) (where t is 1 or 2), —SR_(a), and—S(O)_(t)N(R_(a))₂ (where t is 1 or 2), wherein R_(a) is as describedherein.

Where substituent groups are specified by their conventional chemicalformulae, written from left to right, they equally encompass thechemically identical substituents that would result from writing thestructure from right to left, e.g., —CH₂O— is equivalent to —OCH₂—.

Unless defined otherwise, all technical and scientific terms used hereinhave the same meaning as is commonly understood by one of skill in theart to which this specification pertains.

As used in the specification and claims, the singular form “a”, “an” and“the” includes plural references unless the context clearly dictatesotherwise.

Reference to “about” a value or parameter herein includes (anddescribes) embodiments that are directed to that value or parameter perse. For example, description referring to “about x” includes descriptionof “x” per se. In other instances, the term “about” when used inassociation with other measurements, or used to modify a value, a unit,a constant, or a range of values, refers to variations of between ±0.1%and ±15% of the stated number. For example, in one variation, “about 1”refers to a range between 0.85 and 1.15.

Reference to “between” two values or parameters herein includes (anddescribes) embodiments that include those two values or parameters perse. For example, description referring to “between x and y” includesdescription of “x” and “y” per se.

Representative Examples of Catalysts for Use in ProducingOligosaccharide Compositions

It should be understood that the polymeric catalysts and thesolid-supported catalysts can include any of the Bronsted-Lowry acids,cationic groups, counterions, linkers, hydrophobic groups, cross-linkinggroups, and polymeric backbones or solid supports (as the case may be)described herein, as if each and every combination were listedseparately. For example, in one embodiment, the catalyst can includebenzenesulfonic acid (i.e., a sulfonic acid with a phenyl linker)connected to a polystyrene backbone or attached to the solid support,and an imidazolium chloride connected directly to the polystyrenebackbone or attached directly to the solid support. In anotherembodiment, the polymeric catalyst can include boronyl-benzyl-pyridiniumchloride (i.e., a boronic acid and pyridinium chloride in the samemonomer unit with a phenyl linker) connected to a polystyrene backboneor attached to the solid support. In yet another embodiment, thecatalyst can include benzenesulfonic acid and imidazolium sulfate eachindividually connected to a polyvinyl alcohol backbone or individuallyattached to the solid support.

In some embodiments, the polymeric catalyst is selected from:

-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    nitrate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    nitrate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    iodide-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bromide-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    formate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-nitrate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-chloride-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-bromide-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-iodide-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-bisulfate-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-acetate-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    chloride-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    acetate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    formate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-triphenyl-(4-vinylbenzyl)-phosphonium    chloride-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-triphenyl-(4-vinylbenzyl)-phosphonium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-triphenyl-(4-vinylbenzyl)-phosphonium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-methyl-1-(4-vinylbenzyl)-piperdin-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-methyl-1-(4-vinylbenzyl)-piperdin-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-methyl-1-(4-vinylbenzyl)-piperdin-1-ium    acetate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-4-(4-vinylbenzyl)-morpholine-4-oxide-co-divinyl benzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triethyl-(4-vinylbenzyl)-ammonium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triethyl-(4-vinylbenzyl)-ammonium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triethyl-(4-vinylbenzyl)-ammonium    acetate-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-4-boronyl-1-(4-vinylbenzyl)-pyridinium    chloride-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    nitrate-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylchloride-co-1-methyl-2-vinyl-pyridinium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylchloride-co-1-methyl-2-vinyl-pyridinium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylchloride-co-1-methyl-2-vinyl-pyridinium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-4-(4-vinylbenzyl)-morpholine-4-oxide-co-divinyl benzene];-   poly [styrene-co-4-vinylphenylphosphonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylphenylphosphonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzenel];-   poly [styrene-co-4-vinylphenylphosphonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzenel];-   polylstyrene-co-3-carboxymethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzenel;-   polylstyrene-co-3-carboxymethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzenel;-   polylstyrene-co-3-carboxymethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzenel;-   polylstyrene-co-5-(4-vinylbenzylamino)-isophthalic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzenel;-   polylstyrene-co-5-(4-vinylbenzylamino)-isophthalic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzenel;-   polylstyrene-co-5-(4-vinylbenzylamino)-isophthalic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzenel;-   poly lstyrene-co-(4-vinylbenzylamino)-acetic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzenel;-   poly lstyrene-co-(4-vinylbenzylamino)-acetic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzenel;-   poly lstyrene-co-(4-vinylbenzylamino)-acetic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzenel;-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium    chloride-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenyl phosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium    chloride-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenyl phosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium    bisulfate-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenyl phosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium    bisulfate-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenyl phosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium    acetate-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenyl phosphonium    acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium    acetate-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenyl phosphonium    acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenylphosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenylphosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene)-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium nitrate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(butyl-vinylimidazolium chloride-co-butylimidazolium    bisulfate-co-4-vinylbenzenesulfonic acid);-   poly(butyl-vinylimidazolium bisulfate-co-butylimidazolium    bisulfate-co-4-vinylbenzenesulfonic acid);-   poly(benzyl alcohol-co-4-vinylbenzylalcohol sulfonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzyl    alcohol); and-   poly(benzyl alcohol-co-4-vinylbenzylalcohol sulfonic    acid-co-vinylbenzyltriphenylphosphonium bisulfate-co-divinylbenzyl    alcohol).

In some embodiments, the solid-supported catalyst is selected from:

-   -   amorphous carbon-supported pyrrolium chloride sulfonic acid;    -   amorphous carbon-supported imidazolium chloride sulfonic acid;    -   amorphous carbon-supported pyrazolium chloride sulfonic acid;    -   amorphous carbon-supported oxazolium chloride sulfonic acid;    -   amorphous carbon-supported thiazolium chloride sulfonic acid;    -   amorphous carbon-supported pyridinium chloride sulfonic acid;    -   amorphous carbon-supported pyrimidinium chloride sulfonic acid;    -   amorphous carbon-supported pyrazinium chloride sulfonic acid;    -   amorphous carbon-supported pyridazinium chloride sulfonic acid;    -   amorphous carbon-supported thiazinium chloride sulfonic acid;    -   amorphous carbon-supported morpholinium chloride sulfonic acid;    -   amorphous carbon-supported piperidinium chloride sulfonic acid;    -   amorphous carbon-supported piperizinium chloride sulfonic acid;    -   amorphous carbon-supported pyrollizinium chloride sulfonic acid;    -   amorphous carbon-supported triphenyl phosphonium chloride        sulfonic acid;    -   amorphous carbon-supported trimethyl phosphonium chloride        sulfonic acid;    -   amorphous carbon-supported triethyl phosphonium chloride        sulfonic acid;    -   amorphous carbon-supported tripropyl phosphonium chloride        sulfonic acid;    -   amorphous carbon-supported tributyl phosphonium chloride        sulfonic acid;    -   amorphous carbon-supported trifluoro phosphonium chloride        sulfonic acid;    -   amorphous carbon-supported pyrrolium bromide sulfonic acid;    -   amorphous carbon-supported imidazolium bromide sulfonic acid;    -   amorphous carbon-supported pyrazolium bromide sulfonic acid;    -   amorphous carbon-supported oxazolium bromide sulfonic acid;    -   amorphous carbon-supported thiazolium bromide sulfonic acid;    -   amorphous carbon-supported pyridinium bromide sulfonic acid;    -   amorphous carbon-supported pyrimidinium bromide sulfonic acid;    -   amorphous carbon-supported pyrazinium bromide sulfonic acid;    -   amorphous carbon-supported pyridazinium bromide sulfonic acid;    -   amorphous carbon-supported thiazinium bromide sulfonic acid;    -   amorphous carbon-supported morpholinium bromide sulfonic acid;    -   amorphous carbon-supported piperidinium bromide sulfonic acid;    -   amorphous carbon-supported piperizinium bromide sulfonic acid;    -   amorphous carbon-supported pyrollizinium bromide sulfonic acid;    -   amorphous carbon-supported triphenyl phosphonium bromide        sulfonic acid;    -   amorphous carbon-supported trimethyl phosphonium bromide        sulfonic acid;    -   amorphous carbon-supported triethyl phosphonium bromide sulfonic        acid;    -   amorphous carbon-supported tripropyl phosphonium bromide        sulfonic acid;    -   amorphous carbon-supported tributyl phosphonium bromide sulfonic        acid;    -   amorphous carbon-supported trifluoro phosphonium bromide        sulfonic acid;    -   amorphous carbon-supported pyrrolium bisulfate sulfonic acid;    -   amorphous carbon-supported imidazolium bisulfate sulfonic acid;    -   amorphous carbon-supported pyrazolium bisulfate sulfonic acid;    -   amorphous carbon-supported oxazolium bisulfate sulfonic acid;    -   amorphous carbon-supported thiazolium bisulfate sulfonic acid;    -   amorphous carbon-supported pyridinium bisulfate sulfonic acid;    -   amorphous carbon-supported pyrimidinium bisulfate sulfonic acid;    -   amorphous carbon-supported pyrazinium bisulfate sulfonic acid;    -   amorphous carbon-supported pyridazinium bisulfate sulfonic acid;    -   amorphous carbon-supported thiazinium bisulfate sulfonic acid;    -   amorphous carbon-supported morpholinium bisulfate sulfonic acid;    -   amorphous carbon-supported piperidinium bisulfate sulfonic acid;    -   amorphous carbon-supported piperizinium bisulfate sulfonic acid;    -   amorphous carbon-supported pyrollizinium bisulfate sulfonic        acid;    -   amorphous carbon-supported triphenyl phosphonium bisulfate        sulfonic acid;    -   amorphous carbon-supported trimethyl phosphonium bisulfate        sulfonic acid;    -   amorphous carbon-supported triethyl phosphonium bisulfate        sulfonic acid;    -   amorphous carbon-supported tripropyl phosphonium bisulfate        sulfonic acid;    -   amorphous carbon-supported tributyl phosphonium bisulfate        sulfonic acid;    -   amorphous carbon-supported trifluoro phosphonium bisulfate        sulfonic acid;    -   amorphous carbon-supported pyrrolium formate sulfonic acid;    -   amorphous carbon-supported imidazolium formate sulfonic acid;    -   amorphous carbon-supported pyrazolium formate sulfonic acid;    -   amorphous carbon-supported oxazolium formate sulfonic acid;    -   amorphous carbon-supported thiazolium formate sulfonic acid;    -   amorphous carbon-supported pyridinium formate sulfonic acid;    -   amorphous carbon-supported pyrimidinium formate sulfonic acid;    -   amorphous carbon-supported pyrazinium formate sulfonic acid;    -   amorphous carbon-supported pyridazinium formate sulfonic acid;    -   amorphous carbon-supported thiazinium formate sulfonic acid;    -   amorphous carbon supported morpholinium formate sulfonic acid;    -   amorphous carbon-supported piperidinium formate sulfonic acid;    -   amorphous carbon-supported piperizinium formate sulfonic acid;    -   amorphous carbon-supported pyrollizinium formate sulfonic acid;    -   amorphous carbon-supported triphenyl phosphonium formate        sulfonic acid;    -   amorphous carbon-supported trimethyl phosphonium formate        sulfonic acid;    -   amorphous carbon-supported triethyl phosphonium formate sulfonic        acid;    -   amorphous carbon-supported tripropyl phosphonium formate        sulfonic acid;    -   amorphous carbon-supported tributyl phosphonium formate sulfonic        acid;    -   amorphous carbon-supported trifluoro phosphonium formate        sulfonic acid;    -   amorphous carbon-supported pyrrolium acetate sulfonic acid;    -   amorphous carbon-supported imidazolium acetate sulfonic acid;    -   amorphous carbon-supported pyrazolium acetate sulfonic acid;    -   amorphous carbon-supported oxazolium acetate sulfonic acid;    -   amorphous carbon-supported thiazolium acetate sulfonic acid;    -   amorphous carbon-supported pyridinium acetate sulfonic acid;    -   amorphous carbon-supported pyrimidinium acetate sulfonic acid;    -   amorphous carbon-supported pyrazinium acetate sulfonic acid;    -   amorphous carbon-supported pyridazinium acetate sulfonic acid;    -   amorphous carbon-supported thiazinium acetate sulfonic acid;    -   amorphous carbon-supported morpholinium acetate sulfonic acid;    -   amorphous carbon-supported piperidinium acetate sulfonic acid;    -   amorphous carbon-supported piperizinium acetate sulfonic acid;    -   amorphous carbon-supported pyrollizinium acetate sulfonic acid;    -   amorphous carbon-supported triphenyl phosphonium acetate        sulfonic acid;    -   amorphous carbon-supported trimethyl phosphonium acetate        sulfonic acid;    -   amorphous carbon-supported triethyl phosphonium acetate sulfonic        acid;    -   amorphous carbon-supported tripropyl phosphonium acetate        sulfonic acid;    -   amorphous carbon-supported tributyl phosphonium acetate sulfonic        acid;    -   amorphous carbon-supported trifluoro phosphonium acetate        sulfonic acid;    -   amorphous carbon-supported pyrrolium chloride phosphonic acid;    -   amorphous carbon-supported imidazolium chloride phosphonic acid;    -   amorphous carbon-supported pyrazolium chloride phosphonic acid;    -   amorphous carbon-supported oxazolium chloride phosphonic acid;    -   amorphous carbon-supported thiazolium chloride phosphonic acid;    -   amorphous carbon-supported pyridinium chloride phosphonic acid;    -   amorphous carbon-supported pyrimidinium chloride phosphonic        acid;    -   amorphous carbon-supported pyrazinium chloride phosphonic acid;    -   amorphous carbon-supported pyridazinium chloride phosphonic        acid;    -   amorphous carbon-supported thiazinium chloride phosphonic acid;    -   amorphous carbon-supported morpholinium chloride phosphonic        acid;    -   amorphous carbon-supported piperidinium chloride phosphonic        acid;    -   amorphous carbon-supported piperizinium chloride phosphonic        acid;    -   amorphous carbon-supported pyrollizinium chloride phosphonic        acid;    -   amorphous carbon-supported triphenyl phosphonium chloride        phosphonic acid;    -   amorphous carbon-supported trimethyl phosphonium chloride        phosphonic acid;    -   amorphous carbon-supported triethyl phosphonium chloride        phosphonic acid;    -   amorphous carbon-supported tripropyl phosphonium chloride        phosphonic acid;    -   amorphous carbon-supported tributyl phosphonium chloride        phosphonic acid;    -   amorphous carbon-supported trifluoro phosphonium chloride        phosphonic acid;    -   amorphous carbon-supported pyrrolium bromide phosphonic acid;    -   amorphous carbon-supported imidazolium bromide phosphonic acid;    -   amorphous carbon-supported pyrazolium bromide phosphonic acid;    -   amorphous carbon-supported oxazolium bromide phosphonic acid;    -   amorphous carbon-supported thiazolium bromide phosphonic acid;    -   amorphous carbon-supported pyridinium bromide phosphonic acid;    -   amorphous carbon-supported pyrimidinium bromide phosphonic acid;    -   amorphous carbon-supported pyrazinium bromide phosphonic acid;    -   amorphous carbon-supported pyridazinium bromide phosphonic acid;    -   amorphous carbon-supported thiazinium bromide phosphonic acid;    -   amorphous carbon-supported morpholinium bromide phosphonic acid;    -   amorphous carbon-supported piperidinium bromide phosphonic acid;    -   amorphous carbon-supported piperizinium bromide phosphonic acid;    -   amorphous carbon-supported pyrollizinium bromide phosphonic        acid;    -   amorphous carbon-supported triphenyl phosphonium bromide        phosphonic acid;    -   amorphous carbon-supported trimethyl phosphonium bromide        phosphonic acid;    -   amorphous carbon-supported triethyl phosphonium bromide        phosphonic acid;    -   amorphous carbon-supported tripropyl phosphonium bromide        phosphonic acid;    -   amorphous carbon-supported tributyl phosphonium bromide        phosphonic acid;    -   amorphous carbon-supported trifluoro phosphonium bromide        phosphonic acid;    -   amorphous carbon-supported pyrrolium bisulfate phosphonic acid;    -   amorphous carbon-supported imidazolium bisulfate phosphonic        acid;    -   amorphous carbon-supported pyrazolium bisulfate phosphonic acid;    -   amorphous carbon-supported oxazolium bisulfate phosphonic acid;    -   amorphous carbon-supported thiazolium bisulfate phosphonic acid;    -   amorphous carbon-supported pyridinium bisulfate phosphonic acid;    -   amorphous carbon-supported pyrimidinium bisulfate phosphonic        acid;    -   amorphous carbon-supported pyrazinium bisulfate phosphonic acid;    -   amorphous carbon-supported pyridazinium bisulfate phosphonic        acid;    -   amorphous carbon-supported thiazinium bisulfate phosphonic acid;    -   amorphous carbon-supported morpholinium bisulfate phosphonic        acid;    -   amorphous carbon-supported piperidinium bisulfate phosphonic        acid;    -   amorphous carbon-supported piperizinium bisulfate phosphonic        acid;    -   amorphous carbon-supported pyrollizinium bisulfate phosphonic        acid;    -   amorphous carbon-supported triphenyl phosphonium bisulfate        phosphonic acid;    -   amorphous carbon-supported trimethyl phosphonium bisulfate        phosphonic acid;    -   amorphous carbon-supported triethyl phosphonium bisulfate        phosphonic acid;    -   amorphous carbon-supported tripropyl phosphonium bisulfate        phosphonic acid;    -   amorphous carbon-supported tributyl phosphonium bisulfate        phosphonic acid;    -   amorphous carbon-supported trifluoro phosphonium bisulfate        phosphonic acid;    -   amorphous carbon-supported pyrrolium formate phosphonic acid;    -   amorphous carbon-supported imidazolium formate phosphonic acid;    -   amorphous carbon-supported pyrazolium formate phosphonic acid;    -   amorphous carbon-supported oxazolium formate phosphonic acid;    -   amorphous carbon-supported thiazolium formate phosphonic acid;    -   amorphous carbon-supported pyridinium formate phosphonic acid;    -   amorphous carbon-supported pyrimidinium formate phosphonic acid;    -   amorphous carbon-supported pyrazinium formate phosphonic acid;    -   amorphous carbon-supported pyridazinium formate phosphonic acid;    -   amorphous carbon-supported thiazinium formate phosphonic acid;    -   amorphous carbon-supported morpholinium formate phosphonic acid;    -   amorphous carbon-supported piperidinium formate phosphonic acid;    -   amorphous carbon-supported piperizinium formate phosphonic acid;    -   amorphous carbon-supported pyrollizinium formate phosphonic        acid;    -   amorphous carbon-supported triphenyl phosphonium formate        phosphonic acid;    -   amorphous carbon-supported trimethyl phosphonium formate        phosphonic acid;    -   amorphous carbon-supported triethyl phosphonium formate        phosphonic acid;    -   amorphous carbon-supported tripropyl phosphonium formate        phosphonic acid;    -   amorphous carbon-supported tributyl phosphonium formate        phosphonic acid;    -   amorphous carbon-supported trifluoro phosphonium formate        phosphonic acid;    -   amorphous carbon-supported pyrrolium acetate phosphonic acid;    -   amorphous carbon-supported imidazolium acetate phosphonic acid;    -   amorphous carbon-supported pyrazolium acetate phosphonic acid;    -   amorphous carbon-supported oxazolium acetate phosphonic acid;    -   amorphous carbon-supported thiazolium acetate phosphonic acid;    -   amorphous carbon-supported pyridinium acetate phosphonic acid;    -   amorphous carbon-supported pyrimidinium acetate phosphonic acid;    -   amorphous carbon-supported pyrazinium acetate phosphonic acid;    -   amorphous carbon-supported pyridazinium acetate phosphonic acid;    -   amorphous carbon-supported thiazinium acetate phosphonic acid;    -   amorphous carbon-supported morpholinium acetate phosphonic acid;    -   amorphous carbon-supported piperidinium acetate phosphonic acid;    -   amorphous carbon-supported piperizinium acetate phosphonic acid;    -   amorphous carbon-supported pyrollizinium acetate phosphonic        acid;    -   amorphous carbon-supported triphenyl phosphonium acetate        phosphonic acid;    -   amorphous carbon-supported trimethyl phosphonium acetate        phosphonic acid;    -   amorphous carbon-supported triethyl phosphonium acetate        phosphonic acid;    -   amorphous carbon-supported tripropyl phosphonium acetate        phosphonic acid;    -   amorphous carbon-supported tributyl phosphonium acetate        phosphonic acid;    -   amorphous carbon-supported trifluoro phosphonium acetate        phosphonic acid;    -   amorphous carbon-supported ethanoyl-triphosphonium sulfonic        acid;    -   amorphous carbon-supported ethanoyl-methylmorpholinium sulfonic        acid; and    -   amorphous carbon-supported ethanoyl-imidazolium sulfonic acid.

In other embodiments, the solid-supported catalyst is selected from:

-   -   activated carbon-supported pyrrolium chloride sulfonic acid;    -   activated carbon-supported imidazolium chloride sulfonic acid;    -   activated carbon-supported pyrazolium chloride sulfonic acid;    -   activated carbon-supported oxazolium chloride sulfonic acid;    -   activated carbon-supported thiazolium chloride sulfonic acid;    -   activated carbon-supported pyridinium chloride sulfonic acid;    -   activated carbon-supported pyrimidinium chloride sulfonic acid;    -   activated carbon-supported pyrazinium chloride sulfonic acid;    -   activated carbon-supported pyridazinium chloride sulfonic acid;    -   activated carbon-supported thiazinium chloride sulfonic acid;    -   activated carbon-supported morpholinium chloride sulfonic acid;    -   activated carbon-supported piperidinium chloride sulfonic acid;    -   activated carbon-supported piperizinium chloride sulfonic acid;    -   activated carbon-supported pyrollizinium chloride sulfonic acid;    -   activated carbon-supported triphenyl phosphonium chloride        sulfonic acid;    -   activated carbon-supported trimethyl phosphonium chloride        sulfonic acid;    -   activated carbon-supported triethyl phosphonium chloride        sulfonic acid;    -   activated carbon-supported tripropyl phosphonium chloride        sulfonic acid;    -   activated carbon-supported tributyl phosphonium chloride        sulfonic acid;    -   activated carbon-supported trifluoro phosphonium chloride        sulfonic acid;    -   activated carbon-supported pyrrolium bromide sulfonic acid;    -   activated carbon-supported imidazolium bromide sulfonic acid;    -   activated carbon-supported pyrazolium bromide sulfonic acid;    -   activated carbon-supported oxazolium bromide sulfonic acid;    -   activated carbon-supported thiazolium bromide sulfonic acid;    -   activated carbon-supported pyridinium bromide sulfonic acid;    -   activated carbon-supported pyrimidinium bromide sulfonic acid;    -   activated carbon-supported pyrazinium bromide sulfonic acid;    -   activated carbon-supported pyridazinium bromide sulfonic acid;    -   activated carbon-supported thiazinium bromide sulfonic acid;    -   activated carbon-supported morpholinium bromide sulfonic acid;    -   activated carbon-supported piperidinium bromide sulfonic acid;    -   activated carbon-supported piperizinium bromide sulfonic acid;    -   activated carbon-supported pyrollizinium bromide sulfonic acid;    -   activated carbon-supported triphenyl phosphonium bromide        sulfonic acid;    -   activated carbon-supported trimethyl phosphonium bromide        sulfonic acid;    -   activated carbon-supported triethyl phosphonium bromide sulfonic        acid;    -   activated carbon-supported tripropyl phosphonium bromide        sulfonic acid;    -   activated carbon-supported tributyl phosphonium bromide sulfonic        acid;    -   activated carbon-supported trifluoro phosphonium bromide        sulfonic acid;    -   activated carbon-supported pyrrolium bisulfate sulfonic acid;    -   activated carbon-supported imidazolium bisulfate sulfonic acid;    -   activated carbon-supported pyrazolium bisulfate sulfonic acid;    -   activated carbon-supported oxazolium bisulfate sulfonic acid;    -   activated carbon-supported thiazolium bisulfate sulfonic acid;    -   activated carbon-supported pyridinium bisulfate sulfonic acid;    -   activated carbon-supported pyrimidinium bisulfate sulfonic acid;    -   activated carbon-supported pyrazinium bisulfate sulfonic acid;    -   activated carbon-supported pyridazinium bisulfate sulfonic acid;    -   activated carbon-supported thiazinium bisulfate sulfonic acid;    -   activated carbon-supported morpholinium bisulfate sulfonic acid;    -   activated carbon-supported piperidinium bisulfate sulfonic acid;    -   activated carbon-supported piperizinium bisulfate sulfonic acid;    -   activated carbon-supported pyrollizinium bisulfate sulfonic        acid;    -   activated carbon-supported triphenyl phosphonium bisulfate        sulfonic acid;    -   activated carbon-supported trimethyl phosphonium bisulfate        sulfonic acid;    -   activated carbon-supported triethyl phosphonium bisulfate        sulfonic acid;    -   activated carbon-supported tripropyl phosphonium bisulfate        sulfonic acid;    -   activated carbon-supported tributyl phosphonium bisulfate        sulfonic acid;    -   activated carbon-supported trifluoro phosphonium bisulfate        sulfonic acid;    -   activated carbon-supported pyrrolium formate sulfonic acid;    -   activated carbon-supported imidazolium formate sulfonic acid;    -   activated carbon-supported pyrazolium formate sulfonic acid;    -   activated carbon-supported oxazolium formate sulfonic acid;    -   activated carbon-supported thiazolium formate sulfonic acid;    -   activated carbon-supported pyridinium formate sulfonic acid;    -   activated carbon-supported pyrimidinium formate sulfonic acid;    -   activated carbon-supported pyrazinium formate sulfonic acid;    -   activated carbon-supported pyridazinium formate sulfonic acid;    -   activated carbon-supported thiazinium formate sulfonic acid;    -   activated carbon supported morpholinium formate sulfonic acid;    -   activated carbon-supported piperidinium formate sulfonic acid;    -   activated carbon-supported piperizinium formate sulfonic acid;    -   activated carbon-supported pyrollizinium formate sulfonic acid;    -   activated carbon-supported triphenyl phosphonium formate        sulfonic acid;    -   activated carbon-supported trimethyl phosphonium formate        sulfonic acid;    -   activated carbon-supported triethyl phosphonium formate sulfonic        acid;    -   activated carbon-supported tripropyl phosphonium formate        sulfonic acid;    -   activated carbon-supported tributyl phosphonium formate sulfonic        acid;    -   activated carbon-supported trifluoro phosphonium formate        sulfonic acid;    -   activated carbon-supported pyrrolium acetate sulfonic acid;    -   activated carbon-supported imidazolium acetate sulfonic acid;    -   activated carbon-supported pyrazolium acetate sulfonic acid;    -   activated carbon-supported oxazolium acetate sulfonic acid;    -   activated carbon-supported thiazolium acetate sulfonic acid;    -   activated carbon-supported pyridinium acetate sulfonic acid;    -   activated carbon-supported pyrimidinium acetate sulfonic acid;    -   activated carbon-supported pyrazinium acetate sulfonic acid;    -   activated carbon-supported pyridazinium acetate sulfonic acid;    -   activated carbon-supported thiazinium acetate sulfonic acid;    -   activated carbon-supported morpholinium acetate sulfonic acid;    -   activated carbon-supported piperidinium acetate sulfonic acid;    -   activated carbon-supported piperizinium acetate sulfonic acid;    -   activated carbon-supported pyrollizinium acetate sulfonic acid;    -   activated carbon-supported triphenyl phosphonium acetate        sulfonic acid;    -   activated carbon-supported trimethyl phosphonium acetate        sulfonic acid;    -   activated carbon-supported triethyl phosphonium acetate sulfonic        acid;    -   activated carbon-supported tripropyl phosphonium acetate        sulfonic acid;    -   activated carbon-supported tributyl phosphonium acetate sulfonic        acid;    -   activated carbon-supported trifluoro phosphonium acetate        sulfonic acid;    -   activated carbon-supported pyrrolium chloride phosphonic acid;    -   activated carbon-supported imidazolium chloride phosphonic acid;    -   activated carbon-supported pyrazolium chloride phosphonic acid;    -   activated carbon-supported oxazolium chloride phosphonic acid;    -   activated carbon-supported thiazolium chloride phosphonic acid;    -   activated carbon-supported pyridinium chloride phosphonic acid;    -   activated carbon-supported pyrimidinium chloride phosphonic        acid;    -   activated carbon-supported pyrazinium chloride phosphonic acid;    -   activated carbon-supported pyridazinium chloride phosphonic        acid;    -   activated carbon-supported thiazinium chloride phosphonic acid;    -   activated carbon-supported morpholinium chloride phosphonic        acid;    -   activated carbon-supported piperidinium chloride phosphonic        acid;    -   activated carbon-supported piperizinium chloride phosphonic        acid;    -   activated carbon-supported pyrollizinium chloride phosphonic        acid;    -   activated carbon-supported triphenyl phosphonium chloride        phosphonic acid;    -   activated carbon-supported trimethyl phosphonium chloride        phosphonic acid;    -   activated carbon-supported triethyl phosphonium chloride        phosphonic acid;    -   activated carbon-supported tripropyl phosphonium chloride        phosphonic acid;    -   activated carbon-supported tributyl phosphonium chloride        phosphonic acid;    -   activated carbon-supported trifluoro phosphonium chloride        phosphonic acid;    -   activated carbon-supported pyrrolium bromide phosphonic acid;    -   activated carbon-supported imidazolium bromide phosphonic acid;    -   activated carbon-supported pyrazolium bromide phosphonic acid;    -   activated carbon-supported oxazolium bromide phosphonic acid;    -   activated carbon-supported thiazolium bromide phosphonic acid;    -   activated carbon-supported pyridinium bromide phosphonic acid;    -   activated carbon-supported pyrimidinium bromide phosphonic acid;    -   activated carbon-supported pyrazinium bromide phosphonic acid;    -   activated carbon-supported pyridazinium bromide phosphonic acid;    -   activated carbon-supported thiazinium bromide phosphonic acid;    -   activated carbon-supported morpholinium bromide phosphonic acid;    -   activated carbon-supported piperidinium bromide phosphonic acid;    -   activated carbon-supported piperizinium bromide phosphonic acid;    -   activated carbon-supported pyrollizinium bromide phosphonic        acid;    -   activated carbon-supported triphenyl phosphonium bromide        phosphonic acid;    -   activated carbon-supported trimethyl phosphonium bromide        phosphonic acid;    -   activated carbon-supported triethyl phosphonium bromide        phosphonic acid;    -   activated carbon-supported tripropyl phosphonium bromide        phosphonic acid;    -   activated carbon-supported tributyl phosphonium bromide        phosphonic acid;    -   activated carbon-supported trifluoro phosphonium bromide        phosphonic acid;    -   activated carbon-supported pyrrolium bisulfate phosphonic acid;    -   activated carbon-supported imidazolium bisulfate phosphonic        acid;    -   activated carbon-supported pyrazolium bisulfate phosphonic acid;    -   activated carbon-supported oxazolium bisulfate phosphonic acid;    -   activated carbon-supported thiazolium bisulfate phosphonic acid;    -   activated carbon-supported pyridinium bisulfate phosphonic acid;    -   activated carbon-supported pyrimidinium bisulfate phosphonic        acid;    -   activated carbon-supported pyrazinium bisulfate phosphonic acid;    -   activated carbon-supported pyridazinium bisulfate phosphonic        acid;    -   activated carbon-supported thiazinium bisulfate phosphonic acid;    -   activated carbon-supported morpholinium bisulfate phosphonic        acid;    -   activated carbon-supported piperidinium bisulfate phosphonic        acid;    -   activated carbon-supported piperizinium bisulfate phosphonic        acid;    -   activated carbon-supported pyrollizinium bisulfate phosphonic        acid;    -   activated carbon-supported triphenyl phosphonium bisulfate        phosphonic acid;    -   activated carbon-supported trimethyl phosphonium bisulfate        phosphonic acid;    -   activated carbon-supported triethyl phosphonium bisulfate        phosphonic acid;    -   activated carbon-supported tripropyl phosphonium bisulfate        phosphonic acid;    -   activated carbon-supported tributyl phosphonium bisulfate        phosphonic acid;    -   activated carbon-supported trifluoro phosphonium bisulfate        phosphonic acid;    -   activated carbon-supported pyrrolium formate phosphonic acid;    -   activated carbon-supported imidazolium formate phosphonic acid;    -   activated carbon-supported pyrazolium formate phosphonic acid;    -   activated carbon-supported oxazolium formate phosphonic acid;    -   activated carbon-supported thiazolium formate phosphonic acid;    -   activated carbon-supported pyridinium formate phosphonic acid;    -   activated carbon-supported pyrimidinium formate phosphonic acid;    -   activated carbon-supported pyrazinium formate phosphonic acid;    -   activated carbon-supported pyridazinium formate phosphonic acid;    -   activated carbon-supported thiazinium formate phosphonic acid;    -   activated carbon-supported morpholinium formate phosphonic acid;    -   activated carbon-supported piperidinium formate phosphonic acid;    -   activated carbon-supported piperizinium formate phosphonic acid;    -   activated carbon-supported pyrollizinium formate phosphonic        acid;    -   activated carbon-supported triphenyl phosphonium formate        phosphonic acid;    -   activated carbon-supported trimethyl phosphonium formate        phosphonic acid;    -   activated carbon-supported triethyl phosphonium formate        phosphonic acid;    -   activated carbon-supported tripropyl phosphonium formate        phosphonic acid;    -   activated carbon-supported tributyl phosphonium formate        phosphonic acid;    -   activated carbon-supported trifluoro phosphonium formate        phosphonic acid;    -   activated carbon-supported pyrrolium acetate phosphonic acid;    -   activated carbon-supported imidazolium acetate phosphonic acid;    -   activated carbon-supported pyrazolium acetate phosphonic acid;    -   activated carbon-supported oxazolium acetate phosphonic acid;    -   activated carbon-supported thiazolium acetate phosphonic acid;    -   activated carbon-supported pyridinium acetate phosphonic acid;    -   activated carbon-supported pyrimidinium acetate phosphonic acid;    -   activated carbon-supported pyrazinium acetate phosphonic acid;    -   activated carbon-supported pyridazinium acetate phosphonic acid;    -   activated carbon-supported thiazinium acetate phosphonic acid;    -   activated carbon-supported morpholinium acetate phosphonic acid;    -   activated carbon-supported piperidinium acetate phosphonic acid;    -   activated carbon-supported piperizinium acetate phosphonic acid;    -   activated carbon-supported pyrollizinium acetate phosphonic        acid;    -   activated carbon-supported triphenyl phosphonium acetate        phosphonic acid;    -   activated carbon-supported trimethyl phosphonium acetate        phosphonic acid;    -   activated carbon-supported triethyl phosphonium acetate        phosphonic acid;    -   activated carbon-supported tripropyl phosphonium acetate        phosphonic acid;    -   activated carbon-supported tributyl phosphonium acetate        phosphonic acid;    -   activated carbon-supported trifluoro phosphonium acetate        phosphonic acid;    -   activated carbon-supported ethanoyl-triphosphonium sulfonic        acid;    -   activated carbon-supported ethanoyul-methylmorpholinium sulfonic        acid; and    -   activated carbon-supported ethanoyl-imidazolium sulfonic acid.

Methods to prepare the polymeric and solid-supported catalysts describedherein can be found in WO 2014/031956, which is hereby incorporatedherein specifically with respect to paragraphs [0345]-[3801] and[0382]-[0472].

c) Reaction Conditions for Catalytic Oligosaccharide Formation

In some embodiments, the feed sugar and catalyst (e.g., polymericcatalyst or solid-supported catalyst) are allowed to react for at least1 hour, at least 2 hours, at least 3 hours, at least 4 hours, at least 6hours, at least 8 hours, at least 16 hours, at least 24 hours, at least36 hours, or at least 48 hours; or between 1-24 hours, between 2-12hours, between 3-6 hours, between 1-96 hours, between 12-72 hours, orbetween 12-48 hours.

In some embodiments, the degree of polymerization of the one or moreoligosaccharides produced according to the methods described herein canbe regulated by the reaction time. For example, in some embodiments, thedegree of polymerization of the one or more oligosaccharides isincreased by increasing the reaction time, while in other embodiments,the degree of polymerization of the one or more oligosaccharides isdecreased by decreasing the reaction time.

Reaction Temperature

In some embodiments, the reaction temperature is maintained in the rangeof about 25° C. to about 150° C. In certain embodiments, the temperatureis from about 30° C. to about 125° C., about 60° C. to about 120° C.,about 80° C. to about 115° C., about 90° C. to about 110° C., about 95°C. to about 105° C., or about 100° C. to 110° C.

Amount of Feed Sugar

The amount of the feed sugar used in the methods described hereinrelative to the amount solvent used may affect the rate of reaction andyield. The amount of the feed sugar used may be characterized by the drysolids content. In certain embodiments, dry solids content refers to thetotal solids of a slurry as a percentage on a dry weight basis. In someembodiments, the dry solids content of the feed sugar is between about 5wt % to about 95 wt %, between about 10 wt % to about 80 wt %, betweenabout 15 to about 75 wt %, or between about 15 to about 50 wt %.

Amount of Catalyst

The amount of the catalyst used in the methods described herein maydepend on several factors including, for example, the selection of thetype of feed sugar, the concentration of the feed sugar, and thereaction conditions (e.g., temperature, time, and pH). In someembodiments, the weight ratio of the catalyst to the feed sugar is about0.01 g/g to about 50 g/g, about 0.01 g/g to about 5 g/g, about 0.05 g/gto about 1.0 g/g, about 0.05 g/g to about 0.5 g/g, about 0.05 g/g toabout 0.2 g/g, or about 0.1 g/g to about 0.2 g/g.

Solvent

In certain embodiments, the methods of using the catalyst are carriedout in an aqueous environment. One suitable aqueous solvent is water,which may be obtained from various sources. Generally, water sourceswith lower concentrations of ionic species (e.g., salts of sodium,phosphorous, ammonium, or magnesium) are preferable, as such ionicspecies may reduce effectiveness of the catalyst. In some embodimentswhere the aqueous solvent is water, the water has a resistivity of atleast 0.1 megaohm-centimeters, of at least 1 megaohm-centimeters, of atleast 2 megaohm-centimeters, of at least 5 megaohm-centimeters, or of atleast 10 megaohm-centimeters.

Water Content

Moreover, as the dehydration reaction of the methods progresses, wateris produced with each coupling of the one or more sugars. In certainembodiments, the methods described herein may further include monitoringthe amount of water present in the reaction mixture and/or the ratio ofwater to sugar or catalyst over a period of time. In some embodiments,the method further includes removing at least a portion of waterproduced in the reaction mixture (e.g., by removing at least about anyof 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 97%, 99%, or 100%,such as by vacuum distillation). It should be understood, however, thatthe amount of water to sugar may be adjusted based on the reactionconditions and specific catalyst used.

Any method known in the art may be used to remove water in the reactionmixture, including, for example, by vacuum filtration, vacuumdistillation, heating, and/or evaporation. In some embodiments, themethod comprises including water in the reaction mixture.

In some aspects, provided herein are methods of producing anoligosaccharide composition, by: combining a feed sugar and a catalysthaving acidic and ionic moieties to form a reaction mixture, whereinwater is produced in the reaction mixture; and removing at least aportion of the water produced in the reaction mixture. In certainvariations, at least a portion of water is removed to maintain a watercontent in the reaction mixture of less than 99%, less than 90%, lessthan 80%, less than 70%, less than 60%, less than 50%, less than 40%,less than 30%, less than 20%, less than 10%, less than 5%, or less than1% by weight.

In some embodiments, the degree of polymerization of the one or moreoligosaccharides produced according to the methods described herein canbe regulated by adjusting or controlling the concentration of waterpresent in the reaction mixture. For example, in some embodiments, thedegree of polymerization of the one or more oligosaccharides isincreased by decreasing the water concentration, while in otherembodiments, the degree of polymerization of the one or moreoligosaccharides is decreased by increasing the water concentration. Insome embodiments, the water content of the reaction is adjusted duringthe reaction to regulate the degree of polymerization of the one or moreoligosaccharides produced.

Batch versus Continuous Processing

Generally, the catalyst and the feed sugar are introduced into aninterior chamber of a reactor, either concurrently or sequentially. Thereaction can be performed in a batch process or a continuous process.For example, in one embodiment, method is performed in a batch process,where the contents of the reactor are continuously mixed or blended, andall or a substantial amount of the products of the reaction are removed.In one variation, the method is performed in a batch process, where thecontents of the reactor are initially intermingled or mixed but nofurther physical mixing is performed. In another variation, the methodis performed in a batch process, wherein once further mixing of thecontents, or periodic mixing of the contents of the reactor, isperformed (e.g., at one or more times per hour), all or a substantialamount of the products of the reaction are removed after a certainperiod of time.

In some embodiments, the method is repeated in a sequential batchprocess, wherein at least a portion of the catalyst is separated from atleast a portion of the oligosaccharide composition produced (e.g., asdescribed in more detail infra) and is recycled by further contactingadditional feed sugar.

For example, in one aspect, provided is a method for producing anoligosaccharide composition, by:

-   -   a) combining feed sugar with a catalyst to form a reaction        mixture;        -   wherein the catalyst comprises acidic monomers and ionic            monomers connected to form a polymeric backbone, or        -   wherein the catalyst comprises a solid support, acidic            moieties attached to the solid support, and ionic moieties            attached to the solid support; and    -   b) producing an oligosaccharide composition from at least a        portion of the reaction mixture;    -   c) separating the oligosaccharide composition from the catalyst;    -   d) combining additional feed sugar with the separated catalyst        to form additional reaction mixture; and    -   e) producing additional oligosaccharide composition from at        least a portion of the additional reaction mixture.

In some of embodiments wherein the method is performed in a batchprocess, the catalyst is recycled (e.g., steps (c)-(e) above arerepeated) at least 1, at least 2, at least 3, at least 4, at least 5, atleast 6, at least 7, at least 8, at least 9 or at least 10 times. Insome of these embodiments, the catalyst retains at least 80% activity(e.g., at least 90%, 95%, 96%, 97%, 98%, or 99% activity) after beingrecycled 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 times, when compared to thecatalytic activity under identical conditions prior to being recycled.

In other embodiments, the method is performed in a continuous process,where the contents flow through the reactor with an average continuousflow rate but with no explicit mixing. After introduction of thecatalyst and the feed sugar into the reactor, the contents of thereactor are continuously or periodically mixed or blended, and after aperiod of time, less than all of the products of the reaction areremoved. In one variation, method is performed in a continuous process,where the mixture containing the catalyst and one or more sugars is notactively mixed. Additionally, mixing of catalyst and feed sugar mayoccur as a result of the redistribution of catalysts settling bygravity, or the non-active mixing that occurs as the material flowsthrough a continuous reactor. In some embodiments of the methods, thesteps of combining the feed sugar with a catalyst and isolating theoligosaccharide composition produced are performed concurrently.

Reactors

The reactors used for the methods described herein may be open or closedreactors suitable for use in containing the chemical reactions describedherein. Suitable reactors may include, for example, a fed-batch stirredreactor, a batch stirred reactor, a continuous flow stirred reactor withultrafiltration, a continuous plug-flow column reactor, an attritionreactor, or a reactor with intensive stirring induced by anelectromagnetic field. See e.g., Fernanda de Castilhos Corazza, FlavioFaria de Moraes, Gisella Maria Zanin and Ivo Neitzel, Optimal control infed-batch reactor for the cellobiose hydrolysis, Acta Scientiarum.Technology, 25: 33-38 (2003); Gusakov, A. V., and Sinitsyn, A. P.,Kinetics of the enzymatic hydrolysis of cellulose: 1. A mathematicalmodel for a batch reactor process, Enz. Microb. TechnoL, 7: 346-352(1985); Ryu, S. K., and Lee, J. M., Bioconversion of waste cellulose byusing an attrition bioreactor, Biotechnol. Bioeng. 25: 53-65(1983);Gusakov, A. V., Sinitsyn, A. P., Davydkin, I. Y., Davydkin, V. Y.,Protas, O. V., Enhancement of enzymatic cellulose hydrolysis using anovel type of bioreactor with intensive stirring induced byelectromagnetic field, Appl. Biochem. Biotechnol., 56: 141-153(1996).Other suitable reactor types may include, for example, fluidized bed,upflow blanket, immobilized, and extruder type reactors for hydrolysisand/or fermentation.

In certain embodiments where the method is performed as a continuousprocess, the reactor may include a continuous mixer, such as a screwmixer. The reactors may be generally fabricated from materials that arecapable of withstanding the physical and chemical forces exerted duringthe processes described herein. In some embodiments, such materials usedfor the reactor are capable of tolerating high concentrations of strongliquid acids; however, in other embodiments, such materials may not beresistant to strong acids.

It should also be understood that additional feed sugar and/or catalystmay be added to the reactor, either at the same time or one after theother.

d) Recyclability of Catalysts

The catalysts containing acidic and ionic groups used in the methods ofproducing oligosaccharide compositions as described herein may berecycled. Thus, in one aspect, provided herein are methods of producingoligosaccharide compositions using recyclable catalysts.

Any method known in the art may be used to separate the catalyst forreuse, including, for example, centrifugation, filtration (e.g., vacuumfiltration), and gravity settling.

The methods described herein may be performed as batch or continuousprocesses. Recycling in a batch process may involve, for example,recovering the catalyst from the reaction mixture and reusing therecovered catalyst in one or more subsequent reaction cycles. Recyclingin a continuous process may involve, for example, introducing additionalfeed sugar into the reactor, without additional of fresh catalyst.

In some of embodiments wherein at least a portion of the catalyst isrecycled, the catalyst is recycled at least 1, at least 2, at least 3,at least 4, at least 5, at least 6, at least 7, at least 8, at least 9or at least 10 times. In some of these embodiments, the catalyst retainsat least 80%, at least 90%, at least 95%, at least 96%, at least 97%, atleast 98%, or at least 99% activity after being recycled 1, 2, 3, 4, 5,6, 7, 8, 9 or 10 times, when compared to the catalytic activity underidentical conditions prior to being recycled.

As used herein, the “catalyst activity” refers to the effective firstorder kinetic rate constant for the molar conversion of reactants,k=−ln(1−X(t))/t. The molar conversion of the reactant A at time t isdefined as X_(A)(t)=1-mol(A,t)/mol(A, 0), where mol(A,t) refers to thenumber of moles of species A present in the reaction mixture at time tand mol(A, 0) refers to the number of moles of species A present at thestart of the reaction, t=0. In practice, the number of moles of thereactant A is often measured at several points in time, t₁, t₂, t₃, . .. , t_(n) during a single reaction cycle and used to calculate theconversions X_(A)(t₁), X_(A)(t₂), . . . X_(A)(t_(n)) at thecorresponding times. The first order rate constant k is then calculatedby fitting the data for X_(A)(t).

As used herein, a reaction “cycle” refers to one period of use within asequence of uses of the catalyst. For example, in a batch process, areaction cycle corresponds to the discrete steps of charging a reactorsystem with reactants and catalyst, heating the reaction under suitableconditions to convert the reactants, maintaining the reaction conditionsfor a specified residence time, separating the reaction products fromthe catalyst, and recovering the catalyst for re-use. In a continuousprocess, a cycle refers a single reactor space time during the operationof the continuous process. For example, in a 1,000 liter reactor with acontinuous volumetric flow of 200 liters per hour, the continuousreactor space time is two hours, and the first two hour period ofcontinuous operation is the first reaction cycle, the next two hourperiod of continuous operation is the second reaction cycle, etc.

As used herein, the “loss of activity” or “activity loss” of a catalystis determined by the average fractional reduction in the catalystactivity between consecutive cycles. For example, if the catalystactivity in reaction cycle 1 is k(1) and the catalyst activity inreaction cycle 2 is k(2), then the loss in catalyst activity betweencycle 1 and cycle 2 is calculated as [k(2)−k(1)]/k(1). Over N reactioncycles, the loss of activity is then determined as

${\frac{1}{\left( {N - 1} \right)}\Sigma_{i = 2}^{N}\frac{{k(i)} - {k\left( {i - 1} \right)}}{k(i)}},$measured in units of fractional loss per cycle.

In some variations, the rate constant for the conversion of additionalfeed sugar is less than 20% lower than the rate constant for theconversion of the reactant feed sugar in the first reaction. In certainvariations, the rate constant for conversion of the additional feedsugar is less than 15%, less than 12%, less than 10%, less than 8%, lessthan 6%, less than 4%, less than 2%, or less than 1% lower than the rateconstant for the conversion of the reactant feed sugar in the firstreaction. In some variations, the loss of activity is less than 20% percycle, less than 15% per cycle, less than 10% per cycle, less than 8%per cycle, less than 4% per cycle, less than 2% per cycle, less than 1%per cycle, less than 0.5% per cycle, or less than 0.2% per cycle.

As used herein “catalyst lifetime” refers to the average number ofcycles that a catalyst particle can be re-used before it no longereffectively catalyzes the conversion of additional reactant feed sugar.The catalyst lifetime is calculated as the reciprocal of the loss ofactivity. For example, if the loss of activity is 1% per cycle, then thecatalyst lifetime is 100 cycles. In some variations, the catalystlifetime is at least 1 cycle, at least 2 cycles, at least 10 cycles, atleast 50 cycles, at least 100 cycles, at least 200 cycles, at least 500cycles.

In certain embodiments, a portion of the total mass of the catalyst in areaction may be removed and replaced with fresh catalyst betweenreaction cycles. For example, in some variations, 0.1% of the mass ofthe catalyst may be replaced between reaction cycles, 1% of the mass ofthe catalyst may be replaced between reaction cycles, 2% of the mass ofthe catalyst may be replaced between reaction cycles, 5% of the mass ofthe catalyst may be replaced between reaction cycles, 10% of the mass ofthe catalyst may be replaced between reaction cycles, or 20% of the massof the catalyst may be replaced between reaction cycles.

As used herein, the “catalyst make-up rate” referes to the fraction ofthe catalyst mass that is replaced with fresh catalyst between reactioncycles.

e) Additional Processing Steps

With reference again to FIG. 1 , process 100 may be modified to haveadditional processing steps. Additional processing steps may include,for example, polishing steps. Polishing steps may include, for example,separation, dilution, concentration, filtration, demineralization,chromatographic separation, or decolorization, or any combinationthereof. For example, in one embodiment process 100 is modified toinclude a dilution step and a decolorization step. In another embodimentprocess 100 is modified to include a filtration step and a drying step.

Decolorization

In some embodiments, the methods described herein further include adecolorization step. The one or more oligosaccharides produced mayundergo a decolorization step using any method known in the art,including, for example, treatment with an absorbent, activated carbon,chromatography (e.g., using ion exchange resin), hydrogenation, and/orfiltration (e.g., microfiltration).

In certain embodiments, the one or more oligosaccharides produced arecontacted with a color-absorbing material at a particular temperature,at a particular concentration, and/or for a particular duration of time.In some embodiments, the mass of the color absorbing species contactedwith the one or more oligosaccharides is less than 50% of the mass ofthe one or more oligosaccharides, less than 35% of the mass of the oneor more oligosaccharides, less than 20% of the mass of the one or moreoligosaccharides, less than 10% of the mass of the one or moreoligosaccharides, less than 5% of the mass of the one or moreoligosaccharides, less than 2% of the mass of the one or moreoligosaccharides, or less than 1% of the mass of the one or moreoligosaccharides.

In some embodiments, the one or more oligosaccharides are contacted witha color absorbing material. In certain embodiments, the one or moreoligosaccharides are contacted with a color absorbing material for lessthan 10 hours, less than 5 hours, less than 1 hour, or less than 30minutes. In a particular embodiment, the one or more oligosaccharidesare contacted with a color absorbing material for 1 hour.

In certain embodiments, the one or more oligosaccharides are contactedwith a color absorbing material at a temperature from 20 to 100 degreesCelsius, 30 to 80 degrees Celsius, 40 to 80 degrees Celsius, or 40 to 65degrees Celsius. In a particular embodiment, the one or moreoligosaccharides are contacted with a color absorbing material at atemperature of 50 degrees Celsius.

In certain embodiments, the color absorbing material is activatedcarbon. In one embodiment, the color absorbing material is powderedactivated carbon. In other embodiments, the color absorbing material isan ion exchange resin. In one embodiment, the color absorbing materialis a strong base cationic exchange resin in a chloride form. In anotherembodiment, the color absorbing material is cross-linked polystyrene. Inyet another embodiment, the color absorbing material is cross-linkedpolyacrylate. In certain embodiments, the color absorbing material isAmberlite FPA91, Amberlite FPA98, Dowex 22, Dowex Marathon MSA, or DowexOptipore SD-2.

Demineralization

In some embodiments, the one or more oligosaccharides produced arecontacted with a material to remove salts, minerals, and/or other ionicspecies. In certain embodiments, the one or more oligosaccharides areflowed through an anionic/cationic exchange column pair. In oneembodiment, the anionic exchange column contains a weak base exchangeresin in a hydroxide form and the cationic exchange column contains astrong acid exchange resin in a protonated form.

Separation and Concentration

In some embodiments, the methods described herein further includeisolating the one or more oligosaccharides produced. In certainvariations, isolating the one or more oligosaccharides comprisesseparating at least a portion of the one or more oligosaccharides fromat least a portion of the catalyst, using any method known in the art,including, for example, centrifugation, filtration (e.g., vacuumfiltration, membrane filtration), and gravity settling. In someembodiments, isolating the one or more oligosaccharides comprisesseparating at least a portion of the one or more oligosaccharides fromat least a portion of any unreacted sugar, using any method known in theart, including, for example, filtration (e.g., membrane filtration),chromatography (e.g., chromatographic fractionation), differentialsolubility, and centrifugation (e.g., differential centrifugation).

In some embodiments, the methods described herein further include aconcentration step. For example, in some embodiments, the isolatedoligosaccharides undergo evaporation (e.g., vacuum evaporation) toproduce a concentrated oligosaccharide composition. In otherembodiments, the isolated oligosaccharides undergo a spray drying stepto produce an oligosaccharide powder. In certain embodiments, theisolated oligosaccharides undergo both an evaporation step and a spraydrying step.

f) Bond Refactoring

Feed sugars comprising non-monomeric sugars used in the methodsdescribed herein typically have α-1,4 bonds, and when used as reactantsin the methods described herein, at least a portion of the α-1,4 bondsare converted into α-1,2 bonds, β-1,2 bonds, α-1,3 bonds, β-1,3 bonds,β-1,4 bonds, α-1,6 bonds, and β-1,6 bonds, as applicable. The feedsugars may comprise non-monomeric hexoses or non-monomeric pentoses, ora combination thereof. It should be clear to one of skill in the artthat α-1,6 bonds and β-1,6 bonds may not be applicable to non-monomericpentoses.

Thus, in certain aspects, provided is a method of producing anoligosaccharide composition, by:

combining feed sugar with a catalyst to form a reaction mixture,

-   -   wherein the feed sugar has α-1,4 bonds, and    -   wherein the catalyst has acidic monomers and ionic monomers        connected to form a polymeric backbone, or wherein the catalyst        comprises a solid support, acidic moieties attached to the solid        support, and ionic moieties attached to the solid support; and

converting at least a portion of the α-1,4 bonds in the feed sugar toone or more non-α-1,4 bonds selected from the group consisting of β-1,4bonds, α-1,3 bonds, β-1,3 bonds, α-1,6 bonds, and β-1,6 bonds to producean oligosaccharide composition from at least a portion of the reactionmixture.

It should generally be understood that α-1,4 bonds may also be referredto herein as α(1→4) bonds, and similarly, β-1,4 bonds, α-1,3 bonds,β-1,3 bonds, α-1,6 bonds, and β-1,6 bonds may be referred to as β(1→4),α(1→3), β(1→3), α(1→6), and β(1→6) bonds, respectively. It should alsogenerally be understood that α-1,4 bonds may also be referred to hereinas α-(1,4) glycyosidic linkages, and similarly, β-1,4 bonds, α-1,3bonds, β-1,3 bonds, α-1,6 bonds, and β-1,6 bonds may be referred to asβ-(1,4), α-(1,3), β-(1,3), α-(1,6), and β-(1,6) glycosidic linkages,respectively.

Enumerated Embodiments

The following enumerated embodiments are representative of some aspectsof the invention.

1. An animal feed composition, comprising:

-   -   (i) a base feed, and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   at least 10 mol % α-(1,3) glycosidic linkages; and            -   at least 10 mol %β-(1,3) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            2. The animal feed composition of embodiment 1, wherein the            oligosaccharide composition has a glycosidic bond type            distribution of less than 9 mol % α-(1,4) glycosidic            linkages, and less than 19 mol % α-(1,6) glycosidic            linkages.            3. An animal feed composition, comprising:    -   (i) a base feed, and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   less than 9 mol % α-(1,4) glycosidic linkages; and            -   less than 19 mol % α-(1,6) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            4. The animal feed composition of any one of embodiments 1            to 3, wherein the oligosaccharide composition has a            glycosidic bond type distribution of at least 15 mol %            β-(1,2) glycosidic linkages.            5. The animal feed composition of any one of embodiments 1            to 4, wherein the oligosaccharide composition is present in            the animal feed composition at below 5,000 ppm weight dry            oligosaccharide composition per weight of the animal feed            composition.            6. The animal feed composition of any one of embodiments 1            to 5, wherein the oligosaccharide composition is present in            the animal feed composition at below 3,000 ppm weight dry            oligosaccharide composition per weight of the animal feed            composition.            7. The animal feed composition of any one of embodiments 1            to 6, wherein the oligosaccharide composition is present in            the animal feed composition at between 10 to 1,000 ppm            weight dry oligosaccharide composition per weight of the            animal feed composition.            8. The animal feed composition of any one of embodiments 1            to 7, wherein the oligosaccharide composition is present in            the animal feed composition at between 10 to 500 ppm weight            dry oligosaccharide composition per weight of the animal            feed composition.            9. The animal feed composition of any one of embodiments 1            to 8, wherein the base feed comprises:    -   between 1200 to 1600 cal/lb apparent metabolizable energy;    -   between 16 to 24 wt % crude protein;    -   between 1.0 and 1.4 wt % lysine;    -   between 0.5 and 0.75 wt % methionine;    -   between 0.75 and 1.1 wt % total sulfur amino acids;    -   between 0.7 and 1.0 wt % calcium;    -   between 0.35 and 0.5 wt % total available phosphorous; and    -   between 0.15 and 0.3 wt % sodium.        10. The animal feed composition of any one of embodiments 1 to        9, wherein the oligosaccharide composition comprises an        oligosaccharide selected from the group consisting of a        gluco-oligosaccharide, a galacto-oligosaccharide, a        fructo-oligosaccharide, a manno-oligosaccharide, a        gluco-galacto-oligosaccharide, a gluco-fructo-oligosaccharide, a        gluco-manno-oligosaccharide, a gluco-arabino-oligosaccharide, a        gluco-xylo-oligosaccharide, a galacto-fructo-oligosaccharide, a        galacto-manno-oligosaccharide, a        galacto-arabino-oligosaccharide, a galacto-xylo-oligosaccharide,        a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, and a manno-xylo-oligosaccharide,        or any combinations thereof.        11. The animal feed composition of any one of embodiments 1 to        10, wherein the oligosaccharide composition comprises an        oligosaccharide selected from the group consisting of an        arabino-oligosaccharide, a xylo-oligosaccharide, and an        arabino-xylo-oligosaccharide, or any combinations thereof.        12. The animal feed composition of any one of embodiments 1 to        11, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 0 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages; and    -   between 10 to 55 mol % β-(1,6) glycosidic linkages.        13. The animal feed composition of any one of embodiments 1 to        12, wherein at least 50 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        14. The animal feed composition of any one of embodiments 1 to        13, wherein between 65 and 80 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        15. The animal feed composition of any one of embodiments 1 to        14, wherein at least 50 dry wt % of the oligosaccharide        composition comprises one or more gluco-oligosaccharides.        16. The animal feed composition of any one of embodiments 1 to        14, wherein at least 50 dry wt % of the oligosaccharide        composition comprises one or more        gluco-galacto-oligosaccharides.        17. The animal feed composition of any one of embodiments 1 to        16, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages;    -   between 10 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 9 mol % α-(1,4) glycosidic linkages; and    -   less than 19 mol % α-(1,6) glycosidic linkages.        18. The animal feed composition of any one of embodiments 1 to        16, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 15 mol % α-(1,2) glycosidic linkages;    -   between 0 to 15 mol % β-(1,2) glycosidic linkages;    -   between 1 to 20 mol % α-(1,3) glycosidic linkages;    -   between 1 to 15 mol % β-(1,3) glycosidic linkages;    -   between 5 to 55 mol % β-(1,4) glycosidic linkages;    -   between 15 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages.        19. The animal feed composition of any one of embodiments 1 to        18, wherein the animal feed composition is poultry feed.        20. The animal feed composition of embodiment 19, wherein the        base feed is starter feed.        21. The animal feed composition of any one of embodiments 1 to        20, comprising less than 50 ppm antibiotic.        22. The animal feed composition of any one of embodiments 1 to        21, comprising less than 50 ppm of an ionophore.        23. The animal feed composition of embodiment 21 or 22, wherein        the antibiotic is selected from the group consisting of        bacitracin, bacitracin methylene disalicylate, bacitracin-zinc,        virginiamycin, bambermycin, avilamycin, and efrotomycin, or any        combinations thereof.        24. The animal feed composition of embodiment 22 or 23, wherein        the ionophore is selected from the group consisting of monensin,        salinomycin, narasin, and lasalocid, or any combinations        thereof.        25. The animal feed composition of any one of embodiments 1 to        24, wherein the oligosaccharide composition is a functionalized        oligosaccharide composition.        26. An animal feed pre-mix, comprising:    -   (i) a carrier material; and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   at least 10 mol % α-(1,3) glycosidic linkages; and            -   at least 10 mol % β-(1,3) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            27. The animal feed pre-mix of embodiment 26, wherein the            oligosaccharide composition has a glycosidic bond type            distribution of less than 9 mol % α-(1,4) glycosidic            linkages, and less than 19 mol % α-(1,6) glycosidic            linkages.            28. An animal feed pre-mix, comprising:    -   (i) a carrier material; and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   less than 9 mol % α-(1,4) glycosidic linkages; and            -   less than 19 mol % α-(1,6) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            29. The animal feed composition of any one of embodiments 26            to 28, wherein the oligosaccharide composition has a            glycosidic bond type distribution of at least 15 mol %            β-(1,2) glycosidic linkages.            30. The animal feed pre-mix of any one of embodiments 26 to            29, wherein the animal feed pre-mix comprises at least 10 wt            % dry oligosaccharide composition per weight animal feed            pre-mix.            31. The animal feed pre-mix of any one of embodiments 26 to            30, wherein the animal feed pre-mix comprises between 10 to            60 wt % dry oligosaccharide composition per weight animal            feed pre-mix.            32. The animal feed pre-mix of any one of embodiments 26 to            30, wherein the animal feed pre-mix comprises between 15 to            50 wt % dry oligosaccharide composition per weight animal            feed pre-mix.            33. The animal feed pre-mix of any one of embodiments 26 to            30, wherein the animal feed pre-mix comprises between 20 to            50 dry wt % oligosaccharide composition.            34. The animal feed pre-mix of any one of embodiments 26 to            30, wherein the carrier material is selected from the group            consisting of rice hulls, feed grade silica gel, feed grade            fumed silica, corn gluten feed, corn gluten meal, dried            distiller's grains, and milled corn, or any combinations            thereof.            35. The animal feed pre-mix of any one of embodiments 26 to            34, wherein the carrier material is milled corn.            36. The animal feed pre-mix of any one of embodiments 26 to            35, wherein the moisture content is less than 20 wt %.            37. The animal feed pre-mix of any one of embodiments 26 to            36, wherein the pre-mix is a solid.            38. The animal feed pre-mix of any one of embodiments 26 to            37, wherein the pre-mix is a flowable powder.            39. The animal feed pre-mix of any one of embodiments 26 to            38, wherein the oligosaccharide composition comprises a            gluco-oligosaccharide, a galacto-oligosaccharide, a            fructo-oligosaccharide, a manno-oligosaccharide, a            gluco-galacto-oligosaccharide, a            gluco-fructo-oligosaccharide, a gluco-manno-oligosaccharide,            a gluco-arabino-oligosaccharide, a            gluco-xylo-oligosaccharide, a            galacto-fructo-oligosaccharide, a            galacto-manno-oligosaccharide, a            galacto-arabino-oligosaccharide, a            galacto-xylo-oligosaccharide, a            fructo-manno-oligosaccharide, a            fructo-arabino-oligosaccharide, a            fructo-xylo-oligosaccharide, a            manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide,            or a xylo-gluco-galacto-oligosaccharide, or any combinations            thereof.            40. The animal feed pre-mix of any one of embodiments 26 to            39, wherein the oligosaccharide composition comprises an            oligosaccharide selected from the group consisting of an            arabino-oligosaccharide, a xylo-oligosaccharide, and an            arabino-xylo-oligosaccharide, or any combinations thereof.            41. The animal feed pre-mix of any one of embodiments 26 to            40, wherein the oligosaccharide composition has a glycosidic            bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages; and    -   between 10 to 55 mol % β-(1,6) glycosidic linkages.        42. The animal feed pre-mix of any one of embodiments 26 to 41,        wherein at least 50 dry wt % of the oligosaccharide composition        has a degree of polymerization of at least 3.        43. The animal feed pre-mix of any one of embodiments 26 to 42,        wherein between 65 and 80 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        44. The animal feed pre-mix of any one of embodiments 26 to 43,        wherein at least 50 dry wt % of the oligosaccharide composition        comprises one or more gluco-oligosaccharides.        45. The animal feed pre-mix of any one of embodiments 26 to 44,        wherein at least 50 dry wt % of the oligosaccharide composition        comprises one or more gluco-galacto-oligosaccharides.        46. The animal feed pre-mix of any one of embodiments 26 to 45,        wherein the oligosaccharide composition has a glycosidic bond        type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages;    -   between 10 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 9 mol % α-(1,4) glycosidic linkages; and    -   less than 19 mol % α-(1,6) glycosidic linkages.        47. The animal feed pre-mix of any one of embodiments 26 to 45,        wherein the oligosaccharide composition has a glycosidic bond        type distribution of:    -   between 0 to 15 mol % α-(1,2) glycosidic linkages;    -   between 0 to 15 mol % β-(1,2) glycosidic linkages;    -   between 1 to 20 mol % α-(1,3) glycosidic linkages;    -   between 1 to 15 mol % β-(1,3) glycosidic linkages;    -   between 5 to 55 mol % β-(1,4) glycosidic linkages;    -   between 15 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages.        48. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix reduces feed conversion ratio        (FCR) by between 1 to 10% when fed to an animal as compared to        an animal fed a feed composition without the oligosaccharide        composition.        49. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix reduces FCR by between 1 to 8%        when fed to an animal as compared to an animal fed a feed        composition without the oligosaccharide composition.        50. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix reduces FCR by between 1 to 6%        when fed to an animal as compared to an animal fed a feed        composition without the oligosaccharide composition.        51. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix increases average daily gain by        between 1 to 10% when fed to an animal as compared to an animal        fed a feed composition without the oligosaccharide composition.        52. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix increases average daily gain by        between 1 to 8% when fed to an animal as compared to an animal        fed a feed composition without the oligosaccharide composition.        53. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix increases average daily gain by        between 1 to 6% when fed to an animal as compared to an animal        fed a feed composition without the oligosaccharide composition.        54. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix increases total weight gain by        between 1 to 10% when as compared to an animal fed a feed        composition without the oligosaccharide composition.        55. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix increases total weight gain by        between 1 to 8% when fed to an animal as compared to an animal        fed a feed composition without the oligosaccharide composition.        56. The animal feed pre-mix of any one of embodiments 26 to 47,        wherein the animal feed pre-mix increases total weight gain by        between 1 to 6% when as compared to an animal fed a feed        composition without the oligosaccharide composition.        57. The animal feed pre-mix of any one of embodiments 26 to 56,        wherein the oligosaccharide composition is a functionalized        oligosaccharide composition.        58. An animal feed composition, comprising (i) a base feed        and (ii) the animal feed pre-mix of any one of embodiments 26 to        57.        59. A method of enhancing growth of poultry, comprising:    -   providing feed to poultry, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages;                -   at least 10 mol % β-(1,3) glycosidic linkages; and            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   enhancing growth in the poultry.        60. A method of decreasing feed conversion ratio of feed        provided to poultry, comprising:    -   providing feed to poultry, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   decreasing the feed conversion ratio (FCR) of feed provided to        the poultry.        61. The method of embodiment 59 or 60, wherein the        oligosaccharide composition has a bond distrubtion of at least        15 mol % β-(1,2) glycosidic linkages.        62. The method of any one of embodiments 59 to 61, wherein the        oligosaccharide composition is present in the feed at below        5,000 ppm weight dry oligosaccharide composition per weight of        the feed.        63. The method of any one of embodiments 59 to 61, wherein the        oligosaccharide composition is present in the feed at below        3,000 ppm weight dry oligosaccharide composition per weight of        the feed.        64. The method of any one of embodiments 59 to 61, wherein the        oligosaccharide composition is present in the feed at between 10        to 1,000 ppm weight dry oligosaccharide composition per weight        of the feed.        65. The method of any one of embodiments 59 to 61, wherein the        oligosaccharide composition is present in the feed at between 10        to 500 ppm weight dry oligosaccharide composition per weight of        the feed.        66. The method of any one of embodiments 59 to 65, wherein the        feed conversion ratio (FCR) is between 0 to 4% higher than the        performance target minimum.        67. The method of any one of embodiments 59 to 65, wherein the        feed conversion ratio is decreased by between 0 to 4%.        68. The method of any one of embodiments 59 to 67, wherein the        feed conversion ratio is decreased between 1 to 10% as compared        to poultry provided feed without the oligosaccharide        composition.        69. The method of any one of embodiments 59 to 67, wherein the        feed conversion ratio is decreased between 1 to 8% as compared        to poultry provided feed without the oligosaccharide        composition.        70. The method of any one of embodiments 59 to 67, wherein the        feed conversion ratio is decreased between 1 to 6% as compared        to poultry provided feed without the oligosaccharide        composition.        71. The method of any one of embodiments 68 to 70, wherein the        feed conversion ratio is decreased over 42 days.        72. The method of any one of embodiments 68 to 70, wherein the        feed conversion ratio is decreased over 35 days.        73. The method of any one of embodiments 68 to 70, wherein the        feed conversion ratio is decreased over 6 weeks.        74. The method of any one of embodiments 68 to 70, wherein the        feed conversion ratio is decreased over 6.5 weeks.        75. The method of any one of embodiments 59 to 70, wherein the        poultry are provided feed on a daily basis.        76. The method of any one of embodiments 59 to 70, wherein the        poultry are provided feed on a weekly basis.        77. The method of any one of embodiments 59 to 70, wherein the        poultry are provided feed every other day.        78. The method of any one of embodiments 59 to 77, wherein the        feed is a starter diet.        79. The method of any one of embodiments 59 to 77, wherein the        feed is a grower-type diet.        80. The method of any one of embodiments 59 to 77, wherein the        feed is a finisher-type diet.        81. The method of any one of embodiments 59 to 78, wherein the        feed is provided to the poultry during the starter diet phase.        82. The method of any one of embodiments 59 to 77, 79, and 81,        wherein the feed is provided to the poultry during the grower        diet phase.        83. The method of any one of embodiments 59 to 77, and 80 to 82,        wherein the feed is provided to the poultry during finisher diet        phase.        84. The method of any one of embodiments 59 to 83, wherein the        poultry is broiler chickens, layer hens, or turkeys.        85. The method of any one of embodiments 59 to 84, wherein short        chain fatty acid concentration in the poultry is increased by        between 1 to 80% relative to poultry provided feed without the        oligosaccharide composition.        86. The method of any one of embodiments 59 to 85, wherein short        chain fatty acid concentration in the poultry is increased by        between 10 to 50% relative to poultry provided feed without the        oligosaccharide composition.        87. The method of any one of embodiments 59 to 86, wherein short        chain fatty acid concentration in the poultry is increased by        between 30 to 50% relative to poultry provided feed without the        oligosaccharide composition.        88. The method of any one of embodiments 85 to 87, wherein the        short chain fatty acid concentration is the ileal short chain        fatty acid concentration.        89. The method of any one of embodiments 85 to 87, wherein the        short chain fatty acid concentration is the cecal short chain        fatty acid concentration.        90. The method of any one of embodiments 85 to 89, wherein the        short chain fatty acids comprise butyric acid, propionic acid,        acetic acid, valeric acid, isobutyric acid, isovaleric acid,        2-methyl-butyric acid, or lactic acid, or any combinations        thereof.        91. The method of any one of embodiments 85 to 89, wherein the        short chain fatty acids comprise butyric acid or propionic acid,        or a combination thereof.        92. The method of any one of embodiments 59 to 91, wherein the        poultry is between 0 to 35 days old.        93. The method of any one of embodiments 59 to 91, wherein the        poultry is between 0 to 15 days old.        94. The method of any one of embodiments 59 to 91, wherein the        poultry is between 16 to 28 days old.        95. The method of any one of embodiments 59 to 91, wherein the        poultry is between 29 to 35 days old.        96. The method of any one of embodiments 59 to 91, wherein the        poultry is between 0 to 6 weeks old.        97. The method of any one of embodiments 59 to 91, wherein the        poultry is between 0 to 6.5 weeks old.        98. The method of any one of embodiments 59 to 97, wherein the        poultry has an average daily weight gain, and wherein the        average daily weight gain is at least 50 grams.        99. The method of any one of embodiments 59 to 97, wherein the        poultry has an average daily weight gain, and wherein the        average daily weight gain is at least 2% greater than the        average daily weight gain of poultry provided feed without the        oligosaccharide composition.        100. The method of any one of embodiments 59 to 99, wherein the        poultry has an average weekly weight gain, and wherein the        average weekly weight gain is at least 400 grams.        101. The method of any one of embodiments 59 to 100, wherein the        poultry has an average weekly weight gain, and wherein the        average weekly weight gain is at least 2% greater than poultry        provided feed without the oligosaccharide composition.        102. The method of any one of embodiments 59 to 101, wherein the        poultry has an average final body weight, and wherein the        average final body weight of the poultry is at least 0.05 kg        greater than poultry provided feed without the oligosaccharide        composition.        103. The method of embodiment 97, wherein the poultry is between        1 to 14 days of age, wherein the average daily weight gain is at        least 40 grams.        104. The method of embodiment 97, wherein the poultry is between        14 to 28 days of age, wherein the average daily weight gain is        at least 80 grams.        105. The method of embodiment 97, wherein the poultry is between        29 to 35 days of age, wherein the average daily weight gain is        at least 60 grams.        106. The method of any one of embodiments 103 to 105, wherein        the feed is provided to the poultry on a daily basis.        107. The method of any one of embodiments 59 to 106, further        comprising:    -   processing the poultry to produce a poultry eviscerated carcass,        and    -   obtaining leg meat from the poultry eviscerated carcass,        -   wherein the average yield of leg meat is at least 10% of            live weight.            108. The method of any one of embodiments 59 to 107, further            comprising:    -   processing the poultry to produce a poultry eviscerated carcass,        and    -   obtaining breast meat from the poultry eviscerated carcass,        -   wherein the average yield of breast meat from the poultry is            at least 15% of live weight.            109. The method of any one of embodiments 59 to 108, further            comprising:    -   processing the poultry to produce a poultry eviscerated carcass,        and    -   obtaining drumstick meat from the poultry eviscerated carcass,        -   wherein the average yield of drumstick meat is at least 8%            of live weight.            110. The method of any one of embodiments 59 to 109, further            comprising:    -   processing the poultry to produce a poultry eviscerated carcass,        and    -   obtaining fat from the poultry eviscerated carcass,        -   wherein the average yield of fat is at least 0.5% of live            weight.            111. The method of any one of embodiments 59 to 110, further            comprising:    -   processing the poultry to produce a poultry eviscerated carcass,    -   wherein the average yield of poultry eviscerated carcass is at        least 70% of live weight.        112. The method of any one of embodiments 59 to 111, wherein the        oligosaccharide composition is a functionalized oligosaccharide        composition.        113. The method of any one of embodiments 59 to 112, wherein the        poultry has a disease or disorder.        114. The method of embodiment 113, wherien the disease or        disorder is necrotic enteritis, coccidiosis, nutrient        malabsorption syndrome, intestinal barrier breakdown,        colisepticemia, yolk sack infection, salmonella infection, or        campylobacter infection.        115. The method of embodiment 114, wherein the disease or        disorder is necrotic enteritis.        116. A method of enhancing growth of an animal population,        comprising:    -   feeding to the animal population an animal feed,        -   wherein the animal feed comprises an oligosaccharide            composition at an inclusion rate of less than 5,000 ppm wt %            dry oligosaccharide composition per weight of animal feed;        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   at least 1 mol % α-(1,3) glycosidic linkages; and            -   at least 1 mol % β-(1,3) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3;            and    -   enhancing growth of the animal population.        117. The method of embodiment 116, wherein the oligosaccharide        composition has a glycosidic bond type distrubtion of at least        15 mol % β-(1,2) glycosidic linkages.        118. The method of embodiment 116 or 117, wherein the animal        population is monogastric.        119. The method of any one of embodiments 116 to 118, wherein        the animal population is poultry.        120. The method of any one of embodiments 116 to 119, wherein        the animal is selected from the group consisting of broiler        chickens, layer hens, and turkeys.        121. The method of any one of embodiments 116 to 120, wherein        the feed is provided to the animal population during the starter        diet phase.        122. The method of any one of embodiments 116 to 120, wherein        the feed is provided to the animal population during the grower        diet phase.        123. The method of any one of embodiments 116 to 120, wherein        the feed is provided to the animal population during the        finisher diet phase.        124. The method of any one of embodiments 116 to 123, wherein        the animal feed comprises the oligosaccharide composition at an        inclusion rate of less than 3,000 ppm wt % dry oligosaccharide        composition per weight of animal feed.        125. The method of any one of embodiments 116 to 123, wherein        the animal feed comprises the oligosaccharide composition at an        inclusion rate of between 10 to 1,000 ppm wt % dry        oligosaccharide composition per weight of animal feed.        126. The method of any one of embodiments 116 to 125, wherein        the oligosaccharide composition is a functionalized        oligosaccharide composition.        127. The method of any one of embodiments 116 to 112, wherein        the animal population has a disease or disorder.        128. The method of embodiment 127, wherien the disease or        disorder is necrotic enteritis, coccidiosis, nutrient        malabsorption syndrome, intestinal barrier breakdown,        colisepticemia, yolk sack infection, salmonella infection, or        campylobacter infection.        129. The method of embodiment 128, wherein the disease or        disorder is necrotic enteritis.        130. A composition comprising a plurality of oligosaccharides,        wherein the composition has a glycosidic bond distribution of:    -   at least 1 mol % α-(1,3) glycosidic linkages;    -   at least 1 mol % β-(1,3) glycosidic linkages;    -   at least 15 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages, and    -   wherein at least 10 dry wt % of the oligosaccharide composition        has a degree of polymerization of at least 3.        131. The oligosaccharide composition of embodiment 130,        comprising at least one oligosaccharide selected from the group        consisting of a gluco-oligosaccharide, a        galacto-oligosaccharide, a fructo-oligosaccharide, a        manno-oligosaccharide, an arabino-oligosaccharide, a        xylo-oligosaccharide, a gluco-galacto-oligosaccharide, a        gluco-fructo-oligosaccharide, a gluco-manno-oligosaccharide, a        gluco-arabino-oligosaccharide, a gluco-xylo-oligosaccharide, a        galacto-fructo-oligosaccharide, a galacto-manno-oligosaccharide,        a galacto-arabino-oligosaccharide, a        galacto-xylo-oligosaccharide, a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, an        arabino-xylo-oligosaccharide, and a        xylo-gluco-galacto-oligosaccharide, or any combinations thereof.        132. The oligosaccharide composition of embodiment 130 or 131,        wherein the glycosidic bond distribution is:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages;    -   between 10 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 9 mol % α-(1,4) glycosidic linkages; and    -   less than 19 mol % α-(1,6) glycosidic linkages.        133. The oligosaccharide composition of embodiment 130 or 131,        wherein the glycosidic bond type distribution is:    -   between 0 to 15 mol % α-(1,2) glycosidic linkages;    -   between 0 to 15 mol % β-(1,2) glycosidic linkages;    -   between 1 to 20 mol % α-(1,3) glycosidic linkages;    -   between 1 to 15 mol % β-(1,3) glycosidic linkages;    -   between 5 to 55 mol % β-(1,4) glycosidic linkages;    -   between 15 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages.        134. The oligosaccharide composition of any one of embodiments        130 to 133, comprising less than 50 wt % water.        135. The oligosaccharide composition of any one of embodiments        130 to 134, wherein at least 50 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        136. The oligosaccharide composition of any one of embodiments        130 to 135, wherein between 65 and 80 dry wt % of the        oligosaccharide composition has a degree of polymerization of at        least 3.        137. The oligosaccharide composition of any one of embodiments        130 to 136, wherein the oligosaccharide composition is a        functionalized oligosaccharide composition.        138. A method of producing an animal feed composition,        comprising:    -   combining feed sugar with a catalyst to form a reaction mixture,        -   wherein the catalyst comprises acidic monomers and ionic            monomers connected to form a polymeric backbone, or        -   wherein the catalyst comprises a solid support, acidic            moieties attached to the solid support, and ionic moieties            attached to the solid support; and    -   producing an oligosaccharide composition from at least a portion        of the reaction mixture; and    -   combining the oligosaccharide composition with a base feed to        produce an animal feed composition.        139. The method of embodiment 138, further comprising:    -   separating at least a portion of the catalyst in the reaction        mixture from the oligosaccharide composition produced.        140. The method of embodiment 138, further comprising:    -   combining additional feed sugar with the separated catalyst to        form an additional reaction mixture; and    -   producing an additional oligosaccharide composition from at        least a portion of the additional reaction mixture.        141. The method of any one of embodiments 138 to 140, wherein        the feed sugar comprises glucose, galactose, fructose, mannose,        arabinose, or xylose, or any combinations thereof.        142. The method of any one of embodiments 138 to 141, wherein        the animal feed comprises a gluco-oligosaccharide, a        galacto-oligosaccharide, a fructo-oligosaccharide, a        manno-oligosaccharide, an arabino-oligosaccharide, a        xylo-oligosaccharide, a gluco-galacto-oligosaccharide, a        gluco-fructo-oligosaccharide, a gluco-manno-oligosaccharide, a        gluco-arabino-oligosaccharide, a gluco-xylo-oligosaccharide, a        galacto-fructo-oligosaccharide, a galacto-manno-oligosaccharide,        a galacto-arabino-oligosaccharide, a        galacto-xylo-oligosaccharide, a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, an        arabino-xylo-oligosaccharide, or a        xylo-gluco-galacto-oligosaccharide, or any combinations thereof.        143. The method of any one of embodiments 138 to 141, wherein        the animal feed comprises a galacto-oligosaccharide, a        fructo-oligosaccharide, a manno-oligosaccharide, an        arabino-oligosaccharide, a xylo-oligosaccharide, a        galacto-fructo-oligosaccharide, a galacto-manno-oligosaccharide,        a galacto-arabino-oligosaccharide, a        galacto-xylo-oligosaccharide, a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, or        an arabino-xylo-oligosaccharide, or any combinations thereof.        144. The method of any one of embodiments 138 to 143, wherein        the animal feed composition is poultry feed.        145. The method of any one of embodiments 138 to 143, wherein        the animal feed composition is swine feed.        146. The method of any one of embodiments 138 to 145, wherein        the animal feed composition is in liquid form.        147. The method of any one of embodiments 138 to 145, wherein        the animal feed composition is in solid form.        148. The method of any one of embodiments 138 to 147, wherein        the feed sugar and the catalyst are further combined with one or        more functional groups to form the reaction mixture, and the        oligosaccharide composition produced from at least a portion of        the reaction mixture is a functionalized oligosaccharide        composition.        149. The method of embodiment 148, wherein the one or more        functional groups are amine, hydroxyl, carboxylic acid, sulfur        trioxide, sulfate, or phosphate.        150. The method of embodiment 148, wherein the one or more        functional groups are amines, alcohols, carboxylic acids,        sulfates, phosphates, or sulfur oxides.        151. The method of any one of embodiments 138 to 150, wherein        the catalyst comprises acidic monomers and ionic monomers        connected to form a polymeric backbone.        152. The method of embodiment 151, wherein each acidic monomer        independently comprises at least one Bronsted-Lowry acid.        153. The method of embodiment 152, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        independently selected from the group consisting of sulfonic        acid, phosphonic acid, acetic acid, isophthalic acid, boronic        acid, and perfluorinated acid.        154. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        independently selected from the group consisting of sulfonic        acid and phosphonic acid.        155. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        sulfonic acid.        156. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        phosphonic acid.        157. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is acetic        acid.        158. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        isophthalic acid.        159. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        boronic acid.        160. The method of embodiment 153, wherein the at least one        Bronsted-Lowry acid at each occurrence in the catalyst is        perfluorinated acid.        161. The method of any one of embodiments 151 to 160, wherein        one or more of the acidic monomers are directly connected to the        polymeric backbone.        162. The method of any one of embodiments 151 to 160, wherein        one or more of the acidic monomers each further comprise a        linker connecting the Bronsted-Lowry acid to the polymeric        backbone.        163. The method of embodiment 162, wherein the linker at each        occurrence is independently selected from the group consisting        of unsubstituted or substituted alkylene, unsubstituted or        substituted cycloalkylene, unsubstituted or substituted        alkenylene, unsubstituted or substituted arylene, unsubstituted        or substituted heteroarylene, unsubstituted or substituted        alkylene ether, unsubstituted or substituted alkylene ester, and        unsubstituted or substituted alkylene carbamate.        164. The method of embodiment 162, wherein the Bronsted-Lowry        acid and the linker form a side chain, wherein each side chain        is independently selected from the group consisting of:

165. The method of any one of embodiments 151 to 164, wherein each ionicmonomer independently comprises at least one nitrogen-containingcationic group, at least one phosphorous-containing cationic group, or acombination thereof.166. The method of embodiment 165, wherein the nitrogen-containingcationic group at each occurrence is independently selected from thegroup consisting of pyrrolium, imidazolium, pyrazolium, oxazolium,thiazolium, pyridinium, pyrimidinium, pyrazinium, pyridazinium,thiazinium, morpholinium, piperidinium, piperizinium, and pyrollizinium.167. The method of embodiment 165, wherein the phosphorous-containingcationic group at each occurrence is independently selected from thegroup consisting of triphenyl phosphonium, trimethyl phosphonium,triethyl phosphonium, tripropyl phosphonium, tributyl phosphonium,trichloro phosphonium, and trifluoro phosphonium.168. The method of any one of embodiments 151 to 167, wherein one ormore of the ionic monomers are directly connected to the polymericbackbone.169. The method of any one of embodiments 151 to 167, wherein one ormore of the ionic monomers each further comprise a linker connecting thenitrogen-containing cationic group or the phosphorous-containingcationic group to the polymeric backbone.170. The method of embodiment 169, wherein the linker at each occurrenceis independently selected from the group consisting of unsubstituted orsubstituted alkylene, unsubstituted or substituted cycloalkylene,unsubstituted or substituted alkenylene, unsubstituted or substitutedarylene, unsubstituted or substituted heteroarylene, unsubstituted orsubstituted alkylene ether, unsubstituted or substituted alkylene ester,and unsubstituted or substituted alkylene carbamate.171. The method of embodiment 169, wherein the nitrogen-containingcationic group and the linker form a side chain, wherein each side chainis independently selected from the group consisting of:

172. The method of embodiment 169, wherein the phosphorous-containingcationic group and the linker form a side chain, wherein each side chainis independently selected from the group consisting of:

173. The method of any one of embodiments 151 to 172, wherein thepolymeric backbone is selected from the group consisting ofpolyethylene, polypropylene, polyvinyl alcohol, polystyrene,polyurethane, polyvinyl chloride, polyphenol-aldehyde,polytetrafluoroethylene, polybutylene terephthalate, polycaprolactam,poly(acrylonitrile butadiene styrene), polyalkyleneammonium,polyalkylenediammonium, polyalkylenepyrrolium, polyalkyleneimidazolium,polyalkylenepyrazolium, polyalkyleneoxazolium, polyalkylenethiazolium,polyalkylenepyridinium, polyalkylenepyrimidinium,polyalkylenepyrazinium, polyalkylenepyridazinium,polyalkylenethiazinium, polyalkylenemorpholinium,polyalkylenepiperidinium, polyalkylenepiperizinium,polyalkylenepyrollizinium, polyalkylenetriphenylphosphonium,polyalkylenetrimethylphosphonium, polyalkylenetriethylphosphonium,polyalkylenetripropylphosphonium, polyalkylenetributylphosphonium,polyalkylenetrichlorophosphonium, polyalkylenetrifluorophosphonium, andpolyalkylenediazolium.174. The method of any one of embodiments 151 to 173, further comprisinghydrophobic monomers connected to the polymeric backbone, wherein eachhydrophobic monomer comprises a hydrophobic group.175. The method of embodiment 174, wherein the hydrophobic group at eachoccurrence is independently selected from the group consisting of anunsubstituted or substituted alkyl, an unsubstituted or substitutedcycloalkyl, an unsubstituted or substituted aryl, or an unsubstituted orsubstituted heteroaryl.176. The method of embodiment 174 or 175, wherein the hydrophobic groupis directly connected to the polymeric backbone.177. The method of any one of embodiments 151 to 176, further comprisingacidic-ionic monomers connected to the polymeric backbone, wherein eachacidic-ionic monomer comprises a Bronsted-Lowry acid and a cationicgroup.178. The method of embodiment 177, wherein the cationic group is anitrogen-containing cationic group or a phosphorous-containing cationicgroup.179. The method of embodiment 177 or 178, wherein one or more of theacidic-ionic monomers each further comprise a linker connecting theBronsted-Lowry acid or the cationic group to the polymeric backbone.180. The method of embodiment 179, wherein the linker at each occurrenceis independently selected from the group consisting of unsubstituted orsubstituted alkylene, unsubstituted or substituted cycloalkylene,unsubstituted or substituted alkenylene, unsubstituted or substitutedarylene, unsubstituted or substituted heteroarylene, unsubstituted orsubstituted alkylene ether, unsubstituted or substituted alkylene ester,and unsubstituted or substituted alkylene carbamate.181. The method of embodiment 179, wherein the Bronsted-Lowry acid, thecationic group and the linker form a side chain, wherein each side chainis independently selected from the group consisting of:

182. The method of any one of embodiments 138 to 150, wherein thecatalyst comprises a solid support, acidic moieties attached to thesolid support, and ionic moieties attached to the solid support.183. The method of embodiment 182, wherein the solid support comprises amaterial, wherein the material is selected from the group consisting ofcarbon, silica, silica gel, alumina, magnesia, titania, zirconia, clays,magnesium silicate, silicon carbide, zeolites, ceramics, and anycombinations thereof.184. The method of embodiment 183, wherein the material is selected fromthe group consisting of carbon, magnesia, titania, zirconia, clays,zeolites, ceramics, and any combinations thereof.185. The method of any one of embodiments 182 to 184, wherein eachacidic moiety independently has at least one Bronsted-Lowry acid.186. The method of embodiment 185, wherein each Bronsted-Lowry acid isindependently selected from the group consisting of sulfonic acid,phosphonic acid, acetic acid, isophthalic acid, boronic acid, andperfluorinated acid.187. The method of embodiment 186, wherein each Bronsted-Lowry acid isindependently sulfonic acid or phosphonic acid.188. The method of embodiment 186, wherein each Bronsted-Lowry acid issulfonic acid.189. The method of embodiment 186, wherein each Bronsted-Lowry acid isphosphonic acid.190. The method of embodiment 186, wherein each Bronsted-Lowry acid isacetic acid.191. The method of embodiment 186, wherein each Bronsted-Lowry acid isisophthalic acid.192. The method of embodiment 186, wherein each Bronsted-Lowry acid isboronic acid.193. The method of embodiment 186, wherein each Bronsted-Lowry acid isperfluorinated acid.194. The method of any one of embodiments 182 to 193, wherein one ormore of the acidic moieties are directly attached to the solid support.195. The method of any one of embodiments 182 to 193, wherein one ormore of the acidic moieties are attached to the solid support by alinker.196. The method of embodiment 195, wherein the linker at each occurrenceis independently selected from the group consisting of unsubstituted orsubstituted alkylene, unsubstituted or substituted cycloalkylene,unsubstituted or substituted alkenylene, unsubstituted or substitutedarylene, unsubstituted or substituted heteroarylene, unsubstituted orsubstituted alkylene ether, unsubstituted or substituted alkylene ester,and unsubstituted or substituted alkylene carbamate.197. The method of embodiment 195, wherein each acidic moietyindependently has at least one Bronsted-Lowry acid, wherein theBronsted-Lowry acid and the linker form a side chain, wherein each sidechain is independently selected from the group consisting of:

198. The method of any one of embodiments 182 to 197, wherein each ionicmoiety independently has at least one nitrogen-containing cationic groupor at least one phosphorous-containing cationic group, or a combinationthereof.199. The method of any one of embodiments 182 to 197, wherein each ionicmoiety is selected from the group consisting of pyrrolium, imidazolium,pyrazolium, oxazolium, thiazolium, pyridinium, pyrimidinium, pyrazinium,pyridazinium, thiazinium, morpholinium, piperidinium, piperizinium,pyrollizinium, phosphonium, trimethyl phosphonium, triethyl phosphonium,tripropyl phosphonium, tributyl phosphonium, trichloro phosphonium,triphenyl phosphonium and trifluoro phosphonium.200. The method of any one of embodiments 182 to 197, wherein each ionicmoiety independently has at least one nitrogen-containing cationicgroup, and wherein each nitrogen-containing cationic group isindependently selected from the group consisting of pyrrolium,imidazolium, pyrazolium, oxazolium, thiazolium, pyridinium,pyrimidinium, pyrazinium, pyridazinium, thiazinium, morpholinium,piperidinium, piperizinium, and pyrollizinium.201. The method of any one of embodiments 182 to 197, wherein each ionicmoiety independently has at least one phosphorous-containing cationicgroup, and wherein each phosphorous-containing cationic group isindependently selected from the group consisting of triphenylphosphonium, trimethyl phosphonium, triethyl phosphonium, tripropylphosphonium, tributyl phosphonium, trichloro phosphonium, and trifluorophosphonium.202. The method of any one of embodiments 182 to 201, wherein one ormore of the ionic moieties are directed attached to the solid support.203. The method of any one of embodiments 182 to 201, wherein one ormore of the ionic moieties are attached to the solid support by alinker.204. The method of embodiment 203, wherein each linker is independentlyselected from the group consisting of unsubstituted or substituted alkyllinker, unsubstituted or substituted cycloalkyl linker, unsubstituted orsubstituted alkenyl linker, unsubstituted or substituted aryl linker,unsubstituted or substituted heteroaryl linker, unsubstituted orsubstituted alkyl ether linker, unsubstituted or substituted alkyl esterlinker, and unsubstituted or substituted alkyl carbamate linker.205. The method of embodiment 203, wherein each ionic moietyindependently has at least one nitrogen-containing cationic group,wherein the nitrogen-containing cationic group and the linker form aside chain, wherein each side chain is independently selected from thegroup consisting of:

206. The method of embodiment 203, wherein each ionic moietyindependently has at least one phosphorous-containing cationic group,wherein the phosphorous-containing cationic group and the linker form aside chain, wherein each side chain is independently selected from thegroup consisting of:

207. The method of any one of embodiments, wherein 182 to 206, furthercomprising hydrophobic moieties attached to the solid support.208. The method of embodiment 207, wherein each hydrophobic moiety isselected from the group consisting of an unsubstituted or substitutedalkyl, an unsubstituted or substituted cycloalkyl, an unsubstituted orsubstituted aryl, and an unsubstituted or substituted heteroaryl.209. The method of any one of embodiments 182 to 208, further comprisingacidic-ionic moieties attached to the solid support, wherein eachacidic-ionic moiety comprises a Bronsted-Lowry acid and a cationicgroup.210. The method of embodiment 209, wherein the cationic group is anitrogen-containing cationic group or a phosphorous-containing cationicgroup.211. The method of embodiment 209 or 210, wherein one or more of theacidic-ionic monomers each further comprise a linker connecting theBronsted-Lowry acid or the cationic group to the polymeric backbone.212. The method of embodiment 211, wherein the linker at each occurrenceis independently selected from the group consisting of unsubstituted orsubstituted alkylene, unsubstituted or substituted cycloalkylene,unsubstituted or substituted alkenylene, unsubstituted or substitutedarylene, unsubstituted or substituted heteroarylene, unsubstituted orsubstituted alkylene ether, unsubstituted or substituted alkylene ester,and unsubstituted or substituted alkylene carbamate.213. The method of embodiment 211, wherein the Bronsted-Lowry acid, thecationic group and the linker form a side chain, wherein each side chainis independently selected from the group consisting of:

214. The method of any one of embodiments 182 to 213, wherein thematerial is carbon, and wherein the carbon is selected from the groupconsisting of biochar, amorphous carbon, and activated carbon.215. The method of any one of embodiments 138 to 150, wherein thecatalyst is selected from the group consisting of:

-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    nitrate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-ethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    nitrate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    iodide-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bromide-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-benzoimidazol-1-ium    formate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-nitrate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-chloride-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-bromide-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-iodide-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-bisulfate-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-(4-vinylbenzyl)-pyridinium-acetate-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-4-methyl-4-(4-vinylbenzyl)-morpholin-4-ium    formate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triphenyl-(4-vinylbenzyl)-phosphonium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triphenyl-(4-vinylbenzyl)-phosphonium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triphenyl-(4-vinylbenzyl)-phosphonium    acetate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-methyl-1-(4-vinylbenzyl)-piperdin-1-ium    chloride-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-methyl-1-(4-vinylbenzyl)-piperdin-1-ium    bisulfate-co-divinylbenzene];-   poly[styrene-co-4-vinylbenzenesulfonic    acid-co-1-methyl-1-(4-vinylbenzyl)-piperdin-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-4-(4-vinylbenzyl)-morpholine-4-oxide-co-divinyl benzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triethyl-(4-vinylbenzyl)-ammonium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triethyl-(4-vinylbenzyl)-ammonium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-triethyl-(4-vinylbenzyl)-ammonium    acetate-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-4-boronyl-1-(4-vinylbenzyl)-pyridinium    chloride-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    nitrate-co-1-(4-vinylphenyl)methylphosphonic    acid-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylchloride-co-1-methyl-2-vinyl-pyridinium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylchloride-co-1-methyl-2-vinyl-pyridinium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylchloride-co-1-methyl-2-vinyl-pyridinium    acetate-co-divinylbenzene];-   poly [styrene-co-4-vinylbenzenesulfonic    acid-co-4-(4-vinylbenzyl)-morpholine-4-oxide-co-divinyl benzene];-   poly [styrene-co-4-vinylphenylphosphonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-4-vinylphenylphosphonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-4-vinylphenylphosphonic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-3-carboxymethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-3-carboxymethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-3-carboxymethyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-5-(4-vinylbenzylamino)-isophthalic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-5-(4-vinylbenzylamino)-isophthalic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-5-(4-vinylbenzylamino)-isophthalic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly [styrene-co-(4-vinylbenzylamino)-acetic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    chloride-co-divinylbenzene];-   poly [styrene-co-(4-vinylbenzylamino)-acetic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    bisulfate-co-divinylbenzene];-   poly [styrene-co-(4-vinylbenzylamino)-acetic    acid-co-3-methyl-1-(4-vinylbenzyl)-3H-imidazol-1-ium    acetate-co-divinylbenzene];-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium    chloride-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenyl phosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium    chloride-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenyl phosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium    bisulfate-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenyl phosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium    bisulfate-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenyl phosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium    acetate-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenyl phosphonium    acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium    acetate-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenyl phosphonium    acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenylphosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylmorpholinium    chloride-co-vinylbenzyltriphenylphosphonium    chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylmorpholinium    bisulfate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylmorpholinium    acetate-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene) poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylmethylimidazolium nitrate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzylmethylimidazolium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenesulfonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium    bisulfate-co-divinylbenzene);-   poly(styrene-co-4-vinylbenzenephosphonic    acid-co-vinylbenzyltriphenylphosphonium acetate-co-divinylbenzene);-   poly(butyl-vinylimidazolium chloride-co-butylimidazolium    bisulfate-co-4-vinylbenzenesulfonic acid);-   poly(butyl-vinylimidazolium bisulfate-co-butylimidazolium    bisulfate-co-4-vinylbenzenesulfonic acid);-   poly(benzyl alcohol-co-4-vinylbenzylalcohol sulfonic    acid-co-vinylbenzyltriphenylphosphonium chloride-co-divinylbenzyl    alcohol); and poly(benzyl alcohol-co-4-vinylbenzylalcohol sulfonic    acid-co-vinylbenzyltriphenylphosphonium bisulfate-co-divinylbenzyl    alcohol).    216. The method of any one of embodiments 138 to 150, wherein the    catalyst is selected from the group consisting of:    -   carbon-supported pyrrolium chloride sulfonic acid;    -   carbon-supported imidazolium chloride sulfonic acid;    -   carbon-supported pyrazolium chloride sulfonic acid;    -   carbon-supported oxazolium chloride sulfonic acid;    -   carbon-supported thiazolium chloride sulfonic acid;    -   carbon-supported pyridinium chloride sulfonic acid;    -   carbon-supported pyrimidinium chloride sulfonic acid;    -   carbon-supported pyrazinium chloride sulfonic acid;    -   carbon-supported pyridazinium chloride sulfonic acid;    -   carbon-supported thiazinium chloride sulfonic acid;    -   carbon-supported morpholinium chloride sulfonic acid;    -   carbon-supported piperidinium chloride sulfonic acid;    -   carbon-supported piperizinium chloride sulfonic acid;    -   carbon-supported pyrollizinium chloride sulfonic acid;    -   carbon-supported triphenyl phosphonium chloride sulfonic acid;    -   carbon-supported trimethyl phosphonium chloride sulfonic acid;    -   carbon-supported triethyl phosphonium chloride sulfonic acid;    -   carbon-supported tripropyl phosphonium chloride sulfonic acid;    -   carbon-supported tributyl phosphonium chloride sulfonic acid;    -   carbon-supported trifluoro phosphonium chloride sulfonic acid;    -   carbon-supported pyrrolium bromide sulfonic acid;    -   carbon-supported imidazolium bromide sulfonic acid;    -   carbon-supported pyrazolium bromide sulfonic acid;    -   carbon-supported oxazolium bromide sulfonic acid;    -   carbon-supported thiazolium bromide sulfonic acid;    -   carbon-supported pyridinium bromide sulfonic acid;    -   carbon-supported pyrimidinium bromide sulfonic acid;    -   carbon-supported pyrazinium bromide sulfonic acid;    -   carbon-supported pyridazinium bromide sulfonic acid;    -   carbon-supported thiazinium bromide sulfonic acid;    -   carbon-supported morpholinium bromide sulfonic acid;    -   carbon-supported piperidinium bromide sulfonic acid;    -   carbon-supported piperizinium bromide sulfonic acid;    -   carbon-supported pyrollizinium bromide sulfonic acid;    -   carbon-supported triphenyl phosphonium bromide sulfonic acid;    -   carbon-supported trimethyl phosphonium bromide sulfonic acid;    -   carbon-supported triethyl phosphonium bromide sulfonic acid;    -   carbon-supported tripropyl phosphonium bromide sulfonic acid;    -   carbon-supported tributyl phosphonium bromide sulfonic acid;    -   carbon-supported trifluoro phosphonium bromide sulfonic acid;    -   carbon-supported pyrrolium bisulfate sulfonic acid;    -   carbon-supported imidazolium bisulfate sulfonic acid;    -   carbon-supported pyrazolium bisulfate sulfonic acid;    -   carbon-supported oxazolium bisulfate sulfonic acid;    -   carbon-supported thiazolium bisulfate sulfonic acid;    -   carbon-supported pyridinium bisulfate sulfonic acid;    -   carbon-supported pyrimidinium bisulfate sulfonic acid;    -   carbon-supported pyrazinium bisulfate sulfonic acid;    -   carbon-supported pyridazinium bisulfate sulfonic acid;    -   carbon-supported thiazinium bisulfate sulfonic acid;    -   carbon-supported morpholinium bisulfate sulfonic acid;    -   carbon-supported piperidinium bisulfate sulfonic acid;    -   carbon-supported piperizinium bisulfate sulfonic acid;    -   carbon-supported pyrollizinium bisulfate sulfonic acid;    -   carbon-supported triphenyl phosphonium bisulfate sulfonic acid;    -   carbon-supported trimethyl phosphonium bisulfate sulfonic acid;    -   carbon-supported triethyl phosphonium bisulfate sulfonic acid;    -   carbon-supported tripropyl phosphonium bisulfate sulfonic acid;    -   carbon-supported tributyl phosphonium bisulfate sulfonic acid;    -   carbon-supported trifluoro phosphonium bisulfate sulfonic acid;    -   carbon-supported pyrrolium formate sulfonic acid;    -   carbon-supported imidazolium formate sulfonic acid;    -   carbon-supported pyrazolium formate sulfonic acid;    -   carbon-supported oxazolium formate sulfonic acid;    -   carbon-supported thiazolium formate sulfonic acid;    -   carbon-supported pyridinium formate sulfonic acid;    -   carbon-supported pyrimidinium formate sulfonic acid;    -   carbon-supported pyrazinium formate sulfonic acid;    -   carbon-supported pyridazinium formate sulfonic acid;    -   carbon-supported thiazinium formate sulfonic acid;    -   carbon supported morpholinium formate sulfonic acid;    -   carbon-supported piperidinium formate sulfonic acid;    -   carbon-supported piperizinium formate sulfonic acid;    -   carbon-supported pyrollizinium formate sulfonic acid;    -   carbon-supported triphenyl phosphonium formate sulfonic acid;    -   carbon-supported trimethyl phosphonium formate sulfonic acid;    -   carbon-supported triethyl phosphonium formate sulfonic acid;    -   carbon-supported tripropyl phosphonium formate sulfonic acid;    -   carbon-supported tributyl phosphonium formate sulfonic acid;    -   carbon-supported trifluoro phosphonium formate sulfonic acid;    -   carbon-supported pyrrolium acetate sulfonic acid;    -   carbon-supported imidazolium acetate sulfonic acid;    -   carbon-supported pyrazolium acetate sulfonic acid;    -   carbon-supported oxazolium acetate sulfonic acid;    -   carbon-supported thiazolium acetate sulfonic acid;    -   carbon-supported pyridinium acetate sulfonic acid;    -   carbon-supported pyrimidinium acetate sulfonic acid;    -   carbon-supported pyrazinium acetate sulfonic acid;    -   carbon-supported pyridazinium acetate sulfonic acid;    -   carbon-supported thiazinium acetate sulfonic acid;    -   carbon-supported morpholinium acetate sulfonic acid;    -   carbon-supported piperidinium acetate sulfonic acid;    -   carbon-supported piperizinium acetate sulfonic acid;    -   carbon-supported pyrollizinium acetate sulfonic acid;    -   carbon-supported triphenyl phosphonium acetate sulfonic acid;    -   carbon-supported trimethyl phosphonium acetate sulfonic acid;    -   carbon-supported triethyl phosphonium acetate sulfonic acid;    -   carbon-supported tripropyl phosphonium acetate sulfonic acid;    -   carbon-supported tributyl phosphonium acetate sulfonic acid;    -   carbon-supported trifluoro phosphonium acetate sulfonic acid;    -   carbon-supported pyrrolium chloride phosphonic acid;    -   carbon-supported imidazolium chloride phosphonic acid;    -   carbon-supported pyrazolium chloride phosphonic acid;    -   carbon-supported oxazolium chloride phosphonic acid;    -   carbon-supported thiazolium chloride phosphonic acid;    -   carbon-supported pyridinium chloride phosphonic acid;    -   carbon-supported pyrimidinium chloride phosphonic acid;    -   carbon-supported pyrazinium chloride phosphonic acid;    -   carbon-supported pyridazinium chloride phosphonic acid;    -   carbon-supported thiazinium chloride phosphonic acid;    -   carbon-supported morpholinium chloride phosphonic acid;    -   carbon-supported piperidinium chloride phosphonic acid;    -   carbon-supported piperizinium chloride phosphonic acid;    -   carbon-supported pyrollizinium chloride phosphonic acid;    -   carbon-supported triphenyl phosphonium chloride phosphonic acid;    -   carbon-supported trimethyl phosphonium chloride phosphonic acid;    -   carbon-supported triethyl phosphonium chloride phosphonic acid;    -   carbon-supported tripropyl phosphonium chloride phosphonic acid;    -   carbon-supported tributyl phosphonium chloride phosphonic acid;    -   carbon-supported trifluoro phosphonium chloride phosphonic acid;    -   carbon-supported pyrrolium bromide phosphonic acid;    -   carbon-supported imidazolium bromide phosphonic acid;    -   carbon-supported pyrazolium bromide phosphonic acid;    -   carbon-supported oxazolium bromide phosphonic acid;    -   carbon-supported thiazolium bromide phosphonic acid;    -   carbon-supported pyridinium bromide phosphonic acid;    -   carbon-supported pyrimidinium bromide phosphonic acid;    -   carbon-supported pyrazinium bromide phosphonic acid;    -   carbon-supported pyridazinium bromide phosphonic acid;    -   carbon-supported thiazinium bromide phosphonic acid;    -   carbon-supported morpholinium bromide phosphonic acid;    -   carbon-supported piperidinium bromide phosphonic acid;    -   carbon-supported piperizinium bromide phosphonic acid;    -   carbon-supported pyrollizinium bromide phosphonic acid;    -   carbon-supported triphenyl phosphonium bromide phosphonic acid;    -   carbon-supported trimethyl phosphonium bromide phosphonic acid;    -   carbon-supported triethyl phosphonium bromide phosphonic acid;    -   carbon-supported tripropyl phosphonium bromide phosphonic acid;    -   carbon-supported tributyl phosphonium bromide phosphonic acid;    -   carbon-supported trifluoro phosphonium bromide phosphonic acid;    -   carbon-supported pyrrolium bisulfate phosphonic acid;    -   carbon-supported imidazolium bisulfate phosphonic acid;    -   carbon-supported pyrazolium bisulfate phosphonic acid;    -   carbon-supported oxazolium bisulfate phosphonic acid;    -   carbon-supported thiazolium bisulfate phosphonic acid;    -   carbon-supported pyridinium bisulfate phosphonic acid;    -   carbon-supported pyrimidinium bisulfate phosphonic acid;    -   carbon-supported pyrazinium bisulfate phosphonic acid;    -   carbon-supported pyridazinium bisulfate phosphonic acid;    -   carbon-supported thiazinium bisulfate phosphonic acid;    -   carbon-supported morpholinium bisulfate phosphonic acid;    -   carbon-supported piperidinium bisulfate phosphonic acid;    -   carbon-supported piperizinium bisulfate phosphonic acid;    -   carbon-supported pyrollizinium bisulfate phosphonic acid;    -   carbon-supported triphenyl phosphonium bisulfate phosphonic        acid;    -   carbon-supported trimethyl phosphonium bisulfate phosphonic        acid;    -   carbon-supported triethyl phosphonium bisulfate phosphonic acid;    -   carbon-supported tripropyl phosphonium bisulfate phosphonic        acid;    -   carbon-supported tributyl phosphonium bisulfate phosphonic acid;    -   carbon-supported trifluoro phosphonium bisulfate phosphonic        acid;    -   carbon-supported pyrrolium formate phosphonic acid;    -   carbon-supported imidazolium formate phosphonic acid;    -   carbon-supported pyrazolium formate phosphonic acid;    -   carbon-supported oxazolium formate phosphonic acid;    -   carbon-supported thiazolium formate phosphonic acid;    -   carbon-supported pyridinium formate phosphonic acid;    -   carbon-supported pyrimidinium formate phosphonic acid;    -   carbon-supported pyrazinium formate phosphonic acid;    -   carbon-supported pyridazinium formate phosphonic acid;    -   carbon-supported thiazinium formate phosphonic acid;    -   carbon-supported morpholinium formate phosphonic acid;    -   carbon-supported piperidinium formate phosphonic acid;    -   carbon-supported piperizinium formate phosphonic acid;    -   carbon-supported pyrollizinium formate phosphonic acid;    -   carbon-supported triphenyl phosphonium formate phosphonic acid;    -   carbon-supported trimethyl phosphonium formate phosphonic acid;    -   carbon-supported triethyl phosphonium formate phosphonic acid;    -   carbon-supported tripropyl phosphonium formate phosphonic acid;    -   carbon-supported tributyl phosphonium formate phosphonic acid;    -   carbon-supported trifluoro phosphonium formate phosphonic acid;    -   carbon-supported pyrrolium acetate phosphonic acid;    -   carbon-supported imidazolium acetate phosphonic acid;    -   carbon-supported pyrazolium acetate phosphonic acid;    -   carbon-supported oxazolium acetate phosphonic acid;    -   carbon-supported thiazolium acetate phosphonic acid;    -   carbon-supported pyridinium acetate phosphonic acid;    -   carbon-supported pyrimidinium acetate phosphonic acid;    -   carbon-supported pyrazinium acetate phosphonic acid;    -   carbon-supported pyridazinium acetate phosphonic acid;    -   carbon-supported thiazinium acetate phosphonic acid;    -   carbon-supported morpholinium acetate phosphonic acid;    -   carbon-supported piperidinium acetate phosphonic acid;    -   carbon-supported piperizinium acetate phosphonic acid;    -   carbon-supported pyrollizinium acetate phosphonic acid;    -   carbon-supported triphenyl phosphonium acetate phosphonic acid;    -   carbon-supported trimethyl phosphonium acetate phosphonic acid;    -   carbon-supported triethyl phosphonium acetate phosphonic acid;    -   carbon-supported tripropyl phosphonium acetate phosphonic acid;    -   carbon-supported tributyl phosphonium acetate phosphonic acid;    -   carbon-supported trifluoro phosphonium acetate phosphonic acid;    -   carbon-supported ethanoyl-triphosphonium sulfonic acid;    -   carbon-supported ethanoyl-methylmorpholinium sulfonic acid; and    -   carbon-supported ethanoyl-imidazolium sulfonic acid.        217. The method of any one of embodiments 138 to 216, wherein        the catalyst has a catalyst activity loss of less than 1% per        cycle.        218. The method of any one of embodiments 138 to 217, wherein        the animal feed composition is poultry feed.        219. The method of any one of embodiments 138 to 218, wherein        the animal feed composition is swine feed.        220. A method of increasing weight gain in an animal,        comprising:    -   feeding to the animal an animal feed composition produced        according to the method of any one of embodiments 138 to 219,        wherein the animal feed composition is fed to the animal at an        inclusion rate of less than 500 mg/kg.        221. A method of improving weight gain and reducing feed        conversion ratio of an animal, comprising: feeding to the animal        an animal feed composition produced according to the method of        any one of embodiments 138 to 219.        222. The method of embodiment 218 or 221, wherein the animal is        a chicken. 223. The method of embodiment 218 or 221, wherein the        animal has a disease or disorder.        224. The method of embodiment 223, wherien the disease or        disorder is necrotic enteritis, coccidiosis, nutrient        malabsorption syndrome, intestinal barrier breakdown,        colisepticemia, yolk sack infection, salmonella infection, or        campylobacter infection.        225. The method of embodiment 223, wherein the disease or        disorder is necrotic enteritis.        226. An animal feed composition produced according to the method        of any one of embodiments 138 to 219.        227. An animal feed composition, comprising:    -   an oligosaccharide selected from the group consisting of a        gluco-oligosaccharide, a galacto-oligosaccharide, a        fructo-oligosaccharide, a manno-oligosaccharide, an        arabino-oligosaccharide, a xylo-oligosaccharide, a        gluco-galacto-oligosaccharide, a gluco-fructo-oligosaccharide, a        gluco-manno-oligosaccharide, a gluco-arabino-oligosaccharide, a        gluco-xylo-oligosaccharide, a galacto-fructo-oligosaccharide, a        galacto-manno-oligosaccharide, a        galacto-arabino-oligosaccharide, a galacto-xylo-oligosaccharide,        a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, and        an arabino-xylo-oligosaccharide, or any combinations thereof,        -   wherein the oligosaccharide has a degree of polymerization            of at least 3; and a base feed.            228. The animal feed composition of embodiment 227, wherein            the oligosaccharide composition is a functionalized            oligosaccharide composition.            229. A swine feed composition, comprising:    -   (i) a base feed, and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   at least 10 mol % α-(1,3) glycosidic linkages; and            -   at least 10 mol % β-(1,3) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            230. The swine feed composition of embodiment 229, wherein            the oligosaccharide composition has a glycosidic bond type            distribution of less than 9 mol % α-(1,4) glycosidic            linkages, and less than 19 mol % α-(1,6) glycosidic            linkages.            231. A swine feed composition, comprising:    -   (i) a base feed, and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   less than 9 mol % α-(1,4) glycosidic linkages; and            -   less than 19 mol % α-(1,6) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            232. The swine feed composition of any one of embodiments            229 to 231, wherein the oligosaccharide composition has a            glycosidic bond type distribution of at least 15 mol %            β-(1,2) glycosidic linkages.            233. The swine feed composition of any one of embodiments            229 to 232, wherein the oligosaccharide composition is            present in the swine feed composition at below 5,000 ppm            weight dry oligosaccharide composition per weight of the            swine feed composition.            234. The swine feed composition of any one of embodiments            229 to 233, wherein the oligosaccharide composition            comprises a gluco-oligosaccharide, a            galacto-oligosaccharide, a fructo-oligosaccharide, a            manno-oligosaccharide, a gluco-galacto-oligosaccharide, a            gluco-fructo-oligosaccharide, a gluco-manno-oligosaccharide,            a gluco-arabino-oligosaccharide, a            gluco-xylo-oligosaccharide, a            galacto-fructo-oligosaccharide, a            galacto-manno-oligosaccharide, a            galacto-arabino-oligosaccharide, a            galacto-xylo-oligosaccharide, a            fructo-manno-oligosaccharide, a            fructo-arabino-oligosaccharide, a            fructo-xylo-oligosaccharide, a            manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide,            or a xylo-gluco-galacto-oligosaccharide, or any combinations            thereof.            235. The swine feed composition of any one of embodiments            229 to 233, wherein the oligosaccharide composition            comprises an arabino-oligosaccharide, a            xylo-oligosaccharide, or an arabino-xylo-oligosaccharide, or            any combinations thereof.            236. The swine feed composition of any one of embodiments            229 to 235, wherein the oligosaccharide composition has a            glycosidic bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages; and    -   between 10 to 55 mol % β-(1,6) glycosidic linkages.        237. The swine feed composition of any one of embodiments 229 to        236, wherein at least 50 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        238. The swine feed composition of any one of embodiments 229 to        236, wherein between 65 and 80 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        239. The swine feed composition of any one of embodiments 229 to        236, wherein at least 50 dry wt % of the oligosaccharide        composition comprises one or more gluco-oligosaccharides.        240. The swine feed composition of any one of embodiments 229 to        236, wherein at least 50 dry wt % of the oligosaccharide        composition comprises one or more        gluco-galacto-oligosaccharides.        241. The swine feed composition of any one of embodiments 229 to        240, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages;    -   between 10 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 9 mol % α-(1,4) glycosidic linkages; and    -   less than 19 mol % α-(1,6) glycosidic linkages.        242. The swine feed composition of any one of embodiments 229 to        240, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 15 mol % α-(1,2) glycosidic linkages;    -   between 0 to 15 mol % β-(1,2) glycosidic linkages;    -   between 1 to 20 mol % α-(1,3) glycosidic linkages;    -   between 1 to 15 mol % β-(1,3) glycosidic linkages;    -   between 5 to 55 mol % β-(1,4) glycosidic linkages;    -   between 15 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages.        243. The swine feed composition of any one of embodiments 229 to        242, wherein the oligosaccharide composition is a functionalized        oligosaccharide composition.        244. A swine feed pre-mix, comprising:    -   (i) a carrier material; and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   at least 10 mol % α-(1,3) glycosidic linkages; and            -   at least 10 mol % β-(1,3) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            245. The swine feed pre-mix of embodiment 244, wherein the            oligosaccharide composition has a glycosidic bond type            distribution of less than 9 mol % α-(1,4) glycosidic            linkages, and less than 19 mol % α-(1,6) glycosidic            linkages.            246. A swine feed pre-mix, comprising:    -   (i) a carrier material; and    -   (ii) an oligosaccharide composition,        -   wherein the oligosaccharide composition has a glycosidic            bond type distribution of:            -   less than 9 mol % α-(1,4) glycosidic linkages; and            -   less than 19 mol % α-(1,6) glycosidic linkages, and        -   wherein at least 10 dry wt % of the oligosaccharide            composition has a degree of polymerization of at least 3.            247. The swine feed pre-mix of any one of embodiments 244 to            246, wherein the oligosaccharide composition has a            glycosidic bond type distribution of at least 15 mol %            β-(1,2) glycosidic linkages.            248. The swine feed pre-mix of any one of embodiments 244 to            247, wherein the swine feed pre-mix comprises at least 10 wt            % dry oligosaccharide composition per weight swine feed            pre-mix.            249. The swine feed pre-mix of any one of embodiments 244 to            248, wherein the swine feed pre-mix comprises between 10 to            60 wt % dry oligosaccharide composition per weight swine            feed pre-mix.            250. The swine feed pre-mix of any one of embodiments 244 to            248, wherein the swine feed pre-mix comprises between 15 to            50 wt % dry oligosaccharide composition per weight swine            feed pre-mix.            251. The swine feed pre-mix of any one of embodiments 244 to            248, wherein the swine feed pre-mix comprises between 20 to            50 dry wt % oligosaccharide composition.            252. The swine feed pre-mix of any one of embodiments 244 to            251, wherein the carrier material is selected from the group            consisting of rice hulls, feed grade silica gel, feed grade            fumed silica, corn gluten feed, corn gluten meal, dried            distiller's grains, and milled corn, or any combinations            thereof.            253. The swine feed pre-mix of any one of embodiments 244 to            251, wherein the carrier material is milled corn.            254. The swine feed pre-mix of any one of embodiments 244 to            253, wherein the moisture content is less than 20 wt %.            255. The swine feed pre-mix of any one of embodiments 244 to            255, wherein the pre-mix is a solid.            256. The swine feed pre-mix of any one of embodiments 244 to            255, wherein the pre-mix is a flowable powder.            257. The swine feed pre-mix of any one of embodiments 244 to            256, wherein the oligosaccharide composition comprises a            gluco-oligosaccharide, a galacto-oligosaccharide, a            fructo-oligosaccharide, a manno-oligosaccharide, a            gluco-galacto-oligosaccharide, a            gluco-fructo-oligosaccharide, a gluco-manno-oligosaccharide,            a gluco-arabino-oligosaccharide, a            gluco-xylo-oligosaccharide, a            galacto-fructo-oligosaccharide, a            galacto-manno-oligosaccharide, a            galacto-arabino-oligosaccharide, a            galacto-xylo-oligosaccharide, a            fructo-manno-oligosaccharide, a            fructo-arabino-oligosaccharide, a            fructo-xylo-oligosaccharide, a            manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide,            or a xylo-gluco-galacto-oligosaccharide, or any combinations            thereof.            258. The swine feed pre-mix of any one of embodiments 244 to            256, wherein the oligosaccharide composition comprises an            arabino-oligosaccharide, a xylo-oligosaccharide, or an            arabino-xylo-oligosaccharide, or any combinations thereof.            259. The swine feed pre-mix of any one of embodiments 244 to            258, wherein the oligosaccharide composition has a            glycosidic bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages; and    -   between 10 to 55 mol % β-(1,6) glycosidic linkages.        260. The swine feed pre-mix of any one of embodiments 244 to        259, wherein at least 50 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        261. The swine feed pre-mix of any one of embodiments 244 to        259, wherein between 65 and 80 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        262. The swine feed pre-mix of any one of embodiments 244 to        259, wherein at least 50 dry wt % of the oligosaccharide        composition comprises one or more gluco-oligosaccharides.        263. The swine feed pre-mix of any one of embodiments 244 to        259, wherein at least 50 dry wt % of the oligosaccharide        composition comprises one or more        gluco-galacto-oligosaccharides.        264. The swine feed pre-mix of any one of embodiments 244 to        263, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages;    -   between 10 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 9 mol % α-(1,4) glycosidic linkages; and    -   less than 19 mol % α-(1,6) glycosidic linkages.        265. The swine feed pre-mix of any one of embodiments 244 to        263, wherein the oligosaccharide composition has a glycosidic        bond type distribution of:    -   between 0 to 15 mol % α-(1,2) glycosidic linkages;    -   between 0 to 15 mol % β-(1,2) glycosidic linkages;    -   between 1 to 20 mol % α-(1,3) glycosidic linkages;    -   between 1 to 15 mol % β-(1,3) glycosidic linkages;    -   between 5 to 55 mol % β-(1,4) glycosidic linkages;    -   between 15 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages.        266. The swine feed pre-mix of any one of embodiments 244 to        265, wherein the swine feed pre-mix reduces feed conversion        ratio (FCR) by between 1 to 10% when fed to swine as compared to        a swine fed a feed composition without the oligosaccharide        composition.        267. The swine feed pre-mix of any one of embodiments 244 to        266, wherein the swine feed pre-mix increases average daily gain        by between 1 to 10% when fed to an animal as compared to an        animal fed a feed composition without the oligosaccharide        composition.        268. The swine feed pre-mix of any one of embodiments 244 to        267, wherein the swine feed pre-mix increases total weight gain        by between 1 to 10% when as compared to an animal fed a feed        composition without the oligosaccharide composition.        269. The swine feed pre-mix of any one of embodiments 244 to        268, wherein the oligosaccharide composition is a functionalized        oligosaccharide composition        270. An swine feed composition, comprising (i) a base feed        and (ii) the swine feed pre-mix of any one of embodiments 244 to        269.        271. A method of enhancing growth of swine, comprising:    -   providing feed to swine, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages;                -   at least 10 mol % β-(1,3) glycosidic linkages; and            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   enhancing growth in the swine.        272. A method of decreasing feed conversion ratio of feed        provided to swine, comprising:    -   providing feed to swine, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   decreasing the feed conversion ratio (FCR) of feed provided to        the swine.        273. The method of embodiment 272, wherein the feed conversion        ratio is between 0 to 4% higher than the performance target        minimum.        274. The method of embodiment 272 or 273, wherein the feed        conversion ratio is decreased by between 0 to 4%.        275. The method of any one of embodiments 272 to 274, wherein        the feed conversion ratio is decreased between 1 to 10% as        compared to swine provided feed without the oligosaccharide        composition.        276. The method of any one of embodiments 272 to 274, wherein        the feed conversion ratio is decreased by up to about 15%, about        10%, or about 5%, or between 1% and 15%, between 2% and 15%,        between 3% and 15%, between 4% and 15%, between 5% and 15%,        between 10% and 15%, between 1% and 10%, between 2% and 10%,        between 3% and 10%, between 4% and 10%, between 5% and 10%,        between 2% and 5%, between 2% and 6%, between 2% and 7%, between        2% and 8%, between 2% and 9%, or between 1% and 5%, as compared        to swine fed a feed composition without the oligosaccharide        composition.        277. The method of embodiment 272, wherein the swine suffers        from a disease or a disorder, or is raised in a challenged        environment.        278. The method of embodiment 277, wherein the feed conversion        ratio is decreased by up to about 40%, about 35% about 30%,        about 25%, about 20%, about 15%, about 10%, or about 5%, or        between 1% and 40%, between 5% and 40%, between 10% and 40%,        between 15% and 40%, between 20% and 40%, between 25% and 40%,        between 30% and 40%, between 1% and 30%, between 5% and 30%,        between 10% and 30%, between 5% and 20%, between 10% and 20%,        between 1% and 20%, between 1% and 15%, between 1% and 10%,        between 2% and 10%, between 3% and 10%, between 4% and 10%,        between 5% and 10%, between 2% and 5%, between 2% and 6%,        between 2% and 7%, between 2% and 8%, between 2% and 9%, between        1% and 5%, as compared to swine fed a feed composition without        the oligosaccharide composition.        279. A method of increasing average daily gain in swine,        comprising:    -   providing feed to swine, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   increasing average daily gain in swine.        280. The method of embodiment 279, wherein the average daily        gain is increased by up to about 15%, about 10%, or about 5%, or        between 1% and 15%, between 2% and 15%, between 3% and 15%,        between 4% and 15%, between 5% and 15%, between 10% and 15%,        between 1% and 10%, between 2% and 10%, between 3% and 10%,        between 4% and 10%, between 5% and 10%, between 2% and 5%,        between 2% and 6%, between 2% and 7%, between 2% and 8%, between        2% and 9%, or between 1% and 5%, as compared to swine fed a feed        composition without the oligosaccharide composition.        281. The method of embodiment 280, wherein the swine suffers        from a disease or a disorder, or is raised in a challenged        environment.        282. The method of embodiment 281, wherein the average daily        gain is increased by up to about 40%, about 35% about 30%, about        25%, about 20%, about 15%, about 10%, or about 5%, or between 1%        and 40%, between 5% and 40%, between 10% and 40%, between 15%        and 40%, between 20% and 40%, between 25% and 40%, between 30%        and 40%, between 1% and 30%, between 5% and 30%, between 10% and        30%, between 5% and 20%, between 10% and 20%, between 1% and        20%, between 1% and 15%, between 1% and 10%, between 2% and 10%,        between 3% and 10%, between 4% and 10%, between 5% and 10%,        between 2% and 5%, between 2% and 6%, between 2% and 7%, between        2% and 8%, between 2% and 9%, or between 1% and 5%, as compared        to swine fed a feed composition without the oligosaccharide        composition.        283. A method of increasing average daily feed intake in swine,        comprising:    -   providing feed to swine, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   increasing average daily feed intake in swine.        284. The method of embodiment 283, wherein the average daily        feed intake is increased by up to about 15%, about 10%, or about        5%, or between 1% and 15%, between 2% and 15%, between 3% and        15%, between 4% and 15%, between 5% and 15%, between 10% and        15%, between 1% and 10%, between 2% and 10%, between 3% and 10%,        between 4% and 10%, between 5% and 10%, between 2% and 5%,        between 2% and 6%, between 2% and 7%, between 2% and 8%, between        2% and 9%, or between 1% and 5%, as compared to swine fed a feed        composition without the oligosaccharide composition.        285. The method of embodiment 283, wherein the swine suffers        from a disease or a disorder, or is raised in a challenged        environment.        286. The method of embodiment 285, wherein the average daily        feed intake is increased by up to about 40%, about 35% about        30%, about 25%, about 20%, about 15%, about 10%, or about 5%, or        between 1% and 40%, between 5% and 40%, between 10% and 40%,        between 15% and 40%, between 20% and 40%, between 25% and 40%,        between 30% and 40%, between 1% and 30%, between 5% and 30%,        between 10% and 30%, between 5% and 20%, between 10% and 20%,        between 1% and 20%, between 1% and 15%, between 1% and 10%,        between 2% and 10%, between 3% and 10%, between 4% and 10%,        between 5% and 10%, between 2% and 5%, between 2% and 6%,        between 2% and 7%, between 2% and 8%, between 2% and 9%, or        between 1% and 5%, as compared to swine fed a feed composition        without the oligosaccharide composition.        287. The method of any one of embodiments 271 to 286, wherein        the oligosaccharide composition has a bond distrubtion of at        least 15 mol % β-(1,2) glycosidic linkages.        288. The method of any one of embodiments 271 to 287, wherein        the oligosaccharide composition is present in the feed at below        5,000 ppm weight dry oligosaccharide composition per weight of        the feed.        289. The method of any one of embodiments 271 to 288, wherein        the feed is a nursery diet.        290. The method of any one of embodiments 271 to 288, wherein        the feed is a grower-type diet.        291. The method of any one of embodiments 271 to 288, wherein        the feed is a finisher-type diet.        292. The method of any one of embodiments 271 to 288, wherein        the feed is provided to the swine during the nursery diet phase.        293. The method of any one of embodiments 271 to 292, wherein        the oligosaccharide composition is a functionalized        oligosaccharide composition.        294. The method of any one of embodiments 271 to 293, wherein        the swine has a disease or disorder.        295. The method of any one of embodiments 271 to 294, wherein        the base feed comprises an antibiotic, or wherein the method        further comprising providing an antibiotic to the swine.        296. The method of any one of embodiments 271 to 294, wherein        less than 1,000 ppm, or less than 500 ppm, or less than 100 ppm,        or less than 50 ppm; or between 10 ppm and 200 ppm, or between        50 ppm and 200 ppm, or between 500 ppm and 100 ppm of an        antibiotic is provided to the swine.        297. A method of enhancing growth of poultry, comprising:    -   providing feed to poultry, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages;                -   at least 10 mol % β-(1,3) glycosidic linkages; and            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   enhancing growth in the poultry.        298. A method of decreasing feed conversion ratio of feed        provided to poultry, comprising:    -   providing feed to poultry, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   decreasing the feed conversion ratio (FCR) of feed provided to        the poultry.        299. The method of embodiment 298, wherein the feed conversion        ratio is decreased by up to about 10%, or about 5%, or between        1% and 10%, between 2% and 10%, between 3% and 10%, between 4%        and 10%, between 5% and 10%, between 2% and 5%, between 2% and        6%, between 2% and 7%, between 2% and 8%, between 2% and 9%, or        between 1% and 5%, as compared to poultry fed a feed composition        without the oligosaccharide composition.        300. The method of embodiment 298, wherein the poultry suffers        from a disease or a disorder, or is raised in a challenged        environment.        301. The method of embodiment 300, wherein the feed conversion        ratio is decreased by up to about 30%, about 25%, about 20%,        about 15%, about 10%, or about 5%, or between 1% and 30%,        between 5% and 30%, between 10% and 30%, between 5% and 20%,        between 10% and 20%, between 1% and 20%, between 1% and 15%,        between 1% and 10%, between 2% and 10%, between 3% and 10%,        between 4% and 10%, between 5% and 10%, between 2% and 5%,        between 2% and 6%, between 2% and 7%, between 2% and 8%, between        2% and 9%, or between 1% and 5%, as compared to poultry fed a        feed composition without the oligosaccharide composition.        302. A method of increasing average daily gain in poultry,        comprising:    -   providing feed to poultry, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   increasing average daily gain in poultry.        303. The method of embodiment 302, wherein the average daily        gain is increased by up to about 10%, or about 5%, or between 1%        and 10%, between 2% and 10%, between 3% and 10%, between 4% and        10%, between 5% and 10%, between 2% and 5%, between 2% and 6%,        between 2% and 7%, between 2% and 8%, between 2% and 9%, or        between 1% and 5%, as compared to poultry fed a feed composition        without the oligosaccharide composition.        304. The method of embodiment 302, wherein the poultry suffers        from a disease or a disorder, or is raised in a challenged        environment.        305. The method of embodiment 304, wherein the average daily        gain is increased by up to about 30%, about 25%, about 20%,        about 15%, about 10%, or about 5%, or between 1% and 30%,        between 5% and 30%, between 10% and 30%, between 5% and 20%,        between 10% and 20%, between 1% and 20%, between 1% and 15%,        between 1% and 10%, between 2% and 10%, between 3% and 10%,        between 4% and 10%, between 5% and 10%, between 2% and 5%,        between 2% and 6%, between 2% and 7%, between 2% and 8%, between        2% and 9%, or between 1% and 5%, as compared to poultry fed a        feed composition without the oligosaccharide composition.        306. A method of increasing average daily feed intake in        poultry, comprising:    -   providing feed to poultry, wherein the feed comprises:        -   (i) a base feed; and        -   (ii) an oligosaccharide composition,            -   wherein the oligosaccharide composition has a glycosidic                bond type distribution of:                -   at least 10 mol % α-(1,3) glycosidic linkages; and                -   at least 10 mol % β-(1,3) glycosidic linkages,            -   wherein at least 10 dry wt % of the oligosaccharide                composition has a degree of polymerization of at least                3, and    -   increasing average daily feed intake in poultry.        307. The method of embodiment 306, wherein the average daily        feed intake is increased by up to about 10%, or about 5%, or        between 1% and 10%, between 2% and 10%, between 3% and 10%,        between 4% and 10%, between 5% and 10%, between 2% and 5%,        between 2% and 6%, between 2% and 7%, between 2% and 8%, between        2% and 9%, or between 1% and 5%, as compared to poultry fed a        feed composition without the oligosaccharide composition.        308. The method of embodiment 283, wherein the poultry suffers        from a disease or a disorder, or is raised in a challenged        environment.        309. The method of embodiment 285, wherein the average daily        feed intake is increased by up to about 30%, about 25%, about        20%, about 15%, about 10%, or about 5%, or between 1% and 30%,        between 5% and 30%, between 10% and 30%, between 5% and 20%,        between 10% and 20%, between 1% and 20%, between 1% and 15%,        between 1% and 10%, between 2% and 10%, between 3% and 10%,        between 4% and 10%, between 5% and 10%, between 2% and 5%,        between 2% and 6%, between 2% and 7%, between 2% and 8%, between        2% and 9%, or between 1% and 5%, as compared to poultry fed a        feed composition without the oligosaccharide composition.        310. The method of any one of embodiments 297 to 309, wherein        the oligosaccharide composition has a bond distrubtion of at        least 15 mol % β-(1,2) glycosidic linkages.        311. The method of any one of embodiments 297 to 310, wherein        the oligosaccharide composition is present in the feed at below        5,000 ppm weight dry oligosaccharide composition per weight of        the feed.        312. The method of any one of embodiments 297 to 311, wherein        the oligosaccharide composition is a functionalized        oligosaccharide composition.        313. The method of any one of embodiments 297 to 312, wherein        the poultry has a disease or disorder.        314. The method of any one of embodiments 297 to 313, wherein        the base feed comprises an antibiotic, or wherein the method        further comprising providing an antibiotic to the poultry.        315. The method of any one of embodiments 297 to 314, wherein        less than 1,000 ppm, or less than 500 ppm, or less than 100 ppm,        or less than 50 ppm; or between 10 ppm and 200 ppm, or between        50 ppm and 200 ppm, or between 500 ppm and 100 ppm of an        antibiotic is provided to the poultry.        316. A composition comprising a plurality of oligosaccharides,        wherein the composition has a glycosidic bond distribution of:    -   at least 1 mol % α-(1,3) glycosidic linkages;    -   at least 1 mol % β-(1,3) glycosidic linkages;    -   at least 15 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages, and    -   wherein at least 10 dry wt % of the oligosaccharide composition        has a degree of polymerization of at least 3.        317. The oligosaccharide composition of embodiment 316,        comprising at least one oligosaccharide selected from the group        consisting of a gluco-oligosaccharide, a        galacto-oligosaccharide, a fructo-oligosaccharide, a        manno-oligosaccharide, an arabino-oligosaccharide, a        xylo-oligosaccharide, a gluco-galacto-oligosaccharide, a        gluco-fructo-oligosaccharide, a gluco-manno-oligosaccharide, a        gluco-arabino-oligosaccharide, a gluco-xylo-oligosaccharide, a        galacto-fructo-oligosaccharide, a galacto-manno-oligosaccharide,        a galacto-arabino-oligosaccharide, a        galacto-xylo-oligosaccharide, a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, an        arabino-xylo-oligosaccharide, and a        xylo-gluco-galacto-oligosaccharide, or any combinations thereof.        318. The oligosaccharide composition of embodiment 316 or 317,        wherein the glycosidic bond distribution is:    -   between 0 to 20 mol % α-(1,2) glycosidic linkages;    -   between 10 to 45 mol % β-(1,2) glycosidic linkages;    -   between 1 to 30 mol % α-(1,3) glycosidic linkages;    -   between 1 to 20 mol % β-(1,3) glycosidic linkages;    -   between 0 to 55 mol % β-(1,4) glycosidic linkages;    -   between 10 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 9 mol % α-(1,4) glycosidic linkages; and    -   less than 19 mol % α-(1,6) glycosidic linkages.        319. The oligosaccharide composition of embodiment 316 or 317,        wherein the glycosidic bond type distribution is:    -   between 0 to 15 mol % α-(1,2) glycosidic linkages;    -   between 0 to 15 mol % β-(1,2) glycosidic linkages;    -   between 1 to 20 mol % α-(1,3) glycosidic linkages;    -   between 1 to 15 mol % β-(1,3) glycosidic linkages;    -   between 5 to 55 mol % β-(1,4) glycosidic linkages;    -   between 15 to 55 mol % β-(1,6) glycosidic linkages;    -   less than 20 mol % α-(1,4) glycosidic linkages; and    -   less than 30 mol % α-(1,6) glycosidic linkages.        320. The oligosaccharide composition of any one of embodiments        316 to 319, comprising less than 50 wt % water.        321. The oligosaccharide composition of any one of embodiments        316 to 320, wherein at least 50 dry wt % of the oligosaccharide        composition has a degree of polymerization of at least 3.        322. The oligosaccharide composition of any one of embodiments        316 to 320, wherein between 65 and 80 dry wt % of the        oligosaccharide composition has a degree of polymerization of at        least 3.        323. The oligosaccharide composition of any one of embodiments        316 to 322, wherein the oligosaccharide composition is a        functionalized oligosaccharide composition        324. A method of increasing weight gain in swine, comprising:    -   feeding to the swine a swine feed composition produced according        to the method of any one of embodiments 316 to 323, wherein the        swine feed composition is fed to the swine at an inclusion rate        of less than 5000 mg/kg.        325. A method of improving weight gain and reducing feed        conversion ratio of swine, comprising: feeding to the swine a        swine feed composition produced according to the method of any        one of embodiments 316 to 323.        326. An swine feed composition, comprising:    -   an oligosaccharide selected from the group consisting of a        gluco-oligosaccharide, a galacto-oligosaccharide, a        fructo-oligosaccharide, a manno-oligosaccharide, an        arabino-oligosaccharide, a xylo-oligosaccharide, a        gluco-galacto-oligosaccharide, a gluco-fructo-oligosaccharide, a        gluco-manno-oligosaccharide, a gluco-arabino-oligosaccharide, a        gluco-xylo-oligosaccharide, a galacto-fructo-oligosaccharide, a        galacto-manno-oligosaccharide, a        galacto-arabino-oligosaccharide, a galacto-xylo-oligosaccharide,        a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, an        arabino-xylo-oligosaccharide, and a        xylo-gluco-galacto-oligosaccharide, or any combinations thereof,        -   wherein the oligosaccharide has a degree of polymerization            of at least 3; and a base feed.            327. The swine feed composition of embodiment 294, wherein            the oligosaccharide composition is a functionalized            oligosaccharide composition.            328. An poultry feed composition, comprising:    -   an oligosaccharide selected from the group consisting of a        gluco-oligosaccharide, a galacto-oligosaccharide, a        fructo-oligosaccharide, a manno-oligosaccharide, an        arabino-oligosaccharide, a xylo-oligosaccharide, a        gluco-galacto-oligosaccharide, a gluco-fructo-oligosaccharide, a        gluco-manno-oligosaccharide, a gluco-arabino-oligosaccharide, a        gluco-xylo-oligosaccharide, a galacto-fructo-oligosaccharide, a        galacto-manno-oligosaccharide, a        galacto-arabino-oligosaccharide, a galacto-xylo-oligosaccharide,        a fructo-manno-oligosaccharide, a        fructo-arabino-oligosaccharide, a fructo-xylo-oligosaccharide, a        manno-arabino-oligosaccharide, a manno-xylo-oligosaccharide, an        arabino-xylo-oligosaccharide, and a        xylo-gluco-galacto-oligosaccharide, or any combinations thereof,        -   wherein the oligosaccharide has a degree of polymerization            of at least 3; and a base feed.            329. The poultry feed composition of embodiment 328, wherein            the oligosaccharide composition is a functionalized            oligosaccharide composition.

EXAMPLES

Except where otherwise indicated, commercial reagents were purifiedprior to use following the guidelines of Perrin and Armarego (Perrin, D.D. & Armarego, W. L. F., Purification of Laboratory Chemicals, 3rd ed.;Pergamon Press, Oxford (1988)). Nitrogen gas for use in chemicalreactions was of ultra-pure grade and was dried over phosphorouspentoxide or calcium chloride as required. Unless indicated otherwise,at bench-scale, all non-aqueous reagents were transferred under an inertatmosphere via syringe or Schlenk flask. Where necessary,chromatographic purification of reactants or products was performedusing forced-flow chromatography on 60 mesh silica gel according to themethod described in Still et al., J. Org. Chem., 43: 2923 (1978).Thin-layer chromatography (TLC) was performed using silica-coated glassplates. Visualization of the developed chromatographic plate wasperformed using either Cerium Molybdate (i.e., Hanessian) stain or KMnO₄stain, with gentle heating as required. Fourier-Transform Infrared(FTIR) spectroscopic analysis of solid samples was performed on aPerkin-Elmer 1600 instrument using a horizontal attenuated totalreflectance (ATR) configuration with a zinc selenide crystal.

The moisture content of reagents was determined using a Mettler-ToledoMJ-33 moisture-analyzing balance with a sample size of 0.5-1.0 g. Allmoisture contents were determined as the average percent weight (% wt)loss on drying obtained from triplicate measurements.

The soluble sugar and oligosaccharide content of reaction products wasdetermined by a combination of high performance liquid chromatography(HPLC) and spectrophotometric methods. HPLC determination of solublesugars and oligosaccharides was performed on a Hewlett-Packard 1100Series instrument equipped with a refractive index (RI) detector using a30 cm×7.8 mm BioRad Aminex HPX-87P column with water as the mobilephase. The sugar column was protected by both a lead-exchangedsulfonated-polystyrene guard column and a tri-alkylammoniumhydroxideanionic-exchange guard column. All HPLC samples were microfiltered usinga 0.2 wn syringe filter prior to injection. Sample concentrations weredetermined by reference to calibrations generated from a standardsolution containing glucose, xylose, arabinose, galactose, andgluco-oligosaccharides in known concentrations.

The production of soluble sugar degradation products was determined byhigh performance liquid chromatography (HPLC) on a Hewlett-Packard 1100Series instrument equipped with a refractive index (RI) detector using a30 cm×7.8 mm BioRad Aminex HPX-87H column with 50 mM sulfuric acid asthe mobile phase. The sugar column was protected by both asulfonated-polystyrene guard column and all HPLC samples weremicrofiltered using a 0.2 wn syringe filter prior to injection. Sampleconcentrations were determined by reference to calibrations generatedfrom a standard solution containing formic acid, acetic acid, levulinicacid, 5-hydroxymethylfurfural, and 2-furaldehyde.

The average degree of polymerization (DP) for oligosaccharides wasdetermined as the number average of species containing one, two, three,four, five, six, seven, eight, nine, ten to fifteen, and greater thanfifteen, anhydrosugar monomer units. The relative concentrations ofoligosaccharides corresponding to these different DPs was determined byhigh performance liquid chromatography (HPLC) on a Hewlett-Packard 1100Series instrument equipped with a refractive index (RI) detector using a30 cm×7.8 mm BioRad Aminex HPX-87A column with water as the mobilephase. The analytical column was protected by a silver-coordinated,sulfonated-polystyrene guard column and all HPLC samples weremicrofiltered using a 0.2 pin syringe filter prior to injection.

The conversion X(t) of monomeric (DP1) sugars at time t was determinedaccording to

${{X(t)} = {1 - \frac{{mol}\left( {{DP1},t} \right)}{{mol}\left( {{DP1},0} \right)}}},$where mol(DP1,t) denotes the total moles of monomeric sugars present inthe reaction at time t and mol(DP1,0) denotes the total moles ofmonomeric sugars initially charged to the reaction. Similarly, the yieldto oligosaccharides of a given DP was determined according to

${{Y_{n}(t)} = \frac{{mol}\left( {{DPn},t} \right)}{{mol}\left( {{DP1},0} \right)}},$where mol(DPn,t) denotes the total molar equivalents of species with aDP of n, measured in units of monomeric sugar equivalents. Total yieldto oligosaccharides with DP>1 was determined according to

${Y_{n > 1}(t)} = {\sum_{n > 1}\frac{{mol}\left( {{DPn},t} \right)}{{mol}\left( {{DP1},0} \right)}}$and the total yield to oligosaccharides with DP>2 was determinedaccording to

${{Y_{n > 2}(t)} = {\sum_{n > 2}\frac{{mol}\left( {{DPn},t} \right)}{{mol}\left( {{DP1},0} \right)}}}.$The molar yield to sugar degradation products was determine analogouslyto that for oligosaccharides, where are molar quantities were measuredas monomeric sugar equivalents. Finally, the molar selectivity to agiven product species was determined as the ratio of the species yieldto the sugar conversion, namely S(t)=Y(t)/X(t).

The distribution over glycosidic linkages was determined bytwo-dimensional J-resolved nuclear magnetic resonance (2D-JRES NMR)spectroscopy. Spectra were obtained at room temperature at 400 MHz usingdeuterium oxide as the solvent with trimethylsilyl propanoic acid(TMSP-d4) as the internal reference. Prior to analysis, oligosaccharideswere pre-exchanged by drying the oligosaccharide to constant mass undervacuum at 40 degrees Celsius and redisolving the resulting solid indeuterium oxide. At least two drying/re-disolving cycles were performedfor each sample. For gluco-oligosaccharides andgluco-galacto-oligosaccharides, the abundance of a particular glycosidicbond was determined as the ratio of integrated protons for thatparticular glycosidic bond to the total number of protons integratedover all glycosidic linkages. Proton integral(s) for glycosidic linkageswere determined from the following peak assignments: for α-(1,2)linkages ¹H δ=5.423 and 3.540 ppm; for β-(1,2) linkages ¹H δ=4.649 and3.460 ppm; for α-(1,3) linkages ¹H δ=5.212, 3.850 and 3.760 ppm; forβ-(1,3) linkages ¹H δ=4.750, 4.550, 4.520, 4.503, and 3.502 ppm; forα-(1,4) linkages ¹H δ=5.046 and 3.960 ppm; for β-(1,4) linkages ¹Hδ=4.680, 4.370, 3.890, and 3.410 ppm; for α-(1,6) linkages ¹H δ=5.220,4.960, 4.140, and 3.800 ppm; for β-(1,6) linkages ¹H δ=4.227, 3.610, and3.290 ppm.

The production of undesirable non-carbohydrate bi-products, such aspolyfuranics, solid humins, and other condensation products, wasdetermined by inference from the reaction molar balance. Specifically,the molar yield to undesirable bi-products was determined as thearithmetic difference of the monomeric sugar conversion minus the sum ofthe yields to all quantifiable species. Equivalently, the total molaryield to carbohydrates was determined by hydrolyzing a givenoligosaccharide mixture back to its constituent monomeric sugars underdilute acid conditions at elevated temperature (e.g., incubating at 121degrees Celsius for 1 hour in 2%-4% sulfuric acid) and measuring theresulting moles of monomeric sugars, corrected by a standard monomericcontrol solution that was treated under identical hydrolysis conditions.

The viscosity of oligosaccharide mixtures was determined using aBrookfield viscosometer mounted above a temperature-controlled waterbath used to set the temperature of the solution being measured fromroom temperature up to approximately 95 degrees Celsius. The acidcontent of catalyst samples and aqueous solutions was determined using aHana Instruments 902-C autotitrator with sodium hydroxide as thetitrant, calibrated against a standard solution of potassium hydrogenphthalate (KHP).

Concentration of liquid samples was performed using a Buchi r124 seriesrotary evaporator unit. For oligosaccharide solutions in water, a bathtemperature of approximately 60 degrees Celsius was used. Vacuumpressure of 50-150 mTorr was provided by an oil-immersion pump, whichwas protected by an acetone-dry ice trap to prevent volatilized solventsfrom being drawn into the pump system.

Freeze drying of oligosaccharide samples for analytical analysis wasperformed by coating the walls of a 100 mL round bottom flask (RBF) withapproximately 2 grams of the oligosaccharide solution with a startingconcentration of 60-70 wt % dissolved solids. The loaded flask wasplaced in a −20 degree Celsius freezer for two hours, after which theflask was quickly removed to a room temperature environment andsubjected to a vacuum. A resting pressure of 50-150 mTorr was providedby an oil-immersion pump, which was protected by an acetone-dry ice trapto prevent volatilized solvents from being drawn into the pump system.Typically three sequential freeze-pump cycles were performed.

Example 1 Preparation of Catalyst

This Example demonstrates the preparation and characterization ofpoly-(styrene sulfonic acid-co-vinylbenzylimidazoliumsulfate-co-divinylbenzene).

To a 30 L jacketed glass reactor, housed within a walk-in fume hood andequipped with a 2 inch bottom drain port and a multi-element mixerattached to an overhead air-driven stirrer, was charged 14 L ofN,N-dimethylformamide (DMF, ACS Reagent Grade, Sigma-Aldrich, St. Louis,Mo., USA) and 2.1 kg of 1H-imidazole (ACS Reagent Grade, Sigma-Aldrich,St. Louis, Mo., USA) at room temperature. The DMF was stirred withcontinuous mixing at a stirrer speed of approximately 300 RPM todissolve the imidazole. 7.0 kg of cross-linkedpoly-(styrene-co-divinylbenzene-co-vinylbenzyl chloride) was then addedto the reactor to form a stirred suspension. The reaction mixture washeated to 90 degrees Celsius by pumping heated bath fluid through thereactor jacket, and the resulting heated suspension was maintained for24 hours, after which it was gradually cooled.

The DMF and residual unreacted 1H-imidazole was drained from the resinthrough the bottom port of the reactor, after which the retained resinwas washed repeatedly with acetone to remove any residual heavy solventor unreacted reagents that had become entrained in the resin bed. Thereaction yielded cross-linkedpoly-(styrene-co-divinylbenzene-co-1H-imidazolium chloride) as off-whitespherical resin beads. The resin beads were removed from the reactorthrough the bottom port and heated at 70 degrees Celsius in air to dry.

After being thoroughly cleaned, the 30 L reactor system was charged with2.5 L of 95% sulfuric acid (ACS Reagent Grade) and then approximately 13L of oleum (20% free SO₃ content by weight, Puritan Products, Inc.,Philadelphia, Pa., USA). To the stirred acid solution was graduallyadded 5.1 kg of the cross-linkedpoly-(styrene-co-divinylbenzene-co-1H-imidazolium chloride). After theaddition, the reactor was flushed with dry nitrogen gas, the stirredsuspension was heated to 90 degrees Celsius by pumping heated bath fluidthrough the reactor jacket, and the suspension was maintained at 90degrees Celsius for approximately four hours. After completion of thereaction, the mixture was allowed to cool to approximately 60 degreesCelsius and the residual sulfuric acid mixture was drained from thereactor through the bottom port. After thorough draining, the resin waswashed gradually with 80 wt % sulfuric acid solution and then 60 wt %sulfuric acid solution. Finally the resin was washed repeatedly withdistilled water until the pH of the wash water was above 5.0, asdetermined by pH paper. The resin was removed from the reactor throughthe bottom port to yield the solid catalyst. The acid functional densityof catalyst was determined to be at least 2.0 mmol H+/g dry resin byion-exchange acid-base titration.

Example 2 Preparation of Short Gluco-Oligosaccharides (“GLOS Short”)

This Example demonstrates the preparation of gluco-oligosaccharides fromdextrose using a catalyst with both acidic and ionic groups. Thecatalyst was prepared according to the procedure set forth in Example 1above.

A 22 L jacketed 316L stainless steel reactor (M/DVT-22 mixer/reactorunit, Littleford-Day, Inc., Florence, Ky., USA) was equipped with amixing element comprising four ploughs with an effective diameter ofapproximately 95% that of the reactor clear diameter, a bottom-mounted 2inch diameter outlet port fitted with an 80 mesh stainless steel screenaccessed through a manual ball valve assembly, and a top-mounted 3 inchdiameter inlet port, also accessed through a manual ball valve assembly.Additional fittings provided the ability to inject compressed gases,steam, and to vent the reactor to relieve pressure. The temperature ofthe reactor contents was controlled by flowing heated/chilled oilthrough the reactor jacket and measured via a thermocouple installedalong the internal wall of the reactor cylinder.

The reactor was charged with 1.8 wet kg of catalyst prepared accordingto the procedure described in Example 1 above (moisture content of 44%kg/kg), 5.0 dry kg of food grade dextrose, and 0.2 kg of de-ionizedwater. The reactants were gradually heated to 105° C. with mixingmaintained at 51 rotations of the mixing element per minute. Afterachieving a uniform temperature, hot air at a temperature of 70-90° C.was injected through the bottom port of the reactor and vented throughthe top port. The temperature was increased to 115° C. and mixing wasmaintained for a total of 4 hours.

At the completion of the reaction, approximately 16 kilograms ofdeionized water were added to the reactor and the contents mixed at 60degrees Celsius for 15 minutes to dilute the product mixture. The mixingwas stopped, and the bottom outlet port was opened to collect the liquidproduct, leaving the solid catalyst in the reactor vessel. The reactorwas pressurized to 5 psig using compressed air to aid in thesolid/liquid separation and product recovery. The resulting liquor wasvacuum-filtered through a 0.45 micron polyethersulfone membrane toremove any residual solids, such as fine catalyst particulates, and thenconcentrated to approximately 70 Brix by vacuum rotary evaporation at 50mTorr. The resulting oligosaccharide concentrate was analyzed by HPLC todetermine the product distribution over DP, the extent of formation ofsugar degradation products, and the reaction mass balance closure. Theproduct was determined to contain 67.8% kg/kg DP3+, 12.4% kg/kg DP2,18.4% kg/kg and 1.0% kg/kg sugar caramelization products (levulinicacid, acetic acid, and levoglucosan).

Example 3 Preparation of Long Gluco-Oligosaccharides (“GLOS Long”)

This Example demonstrates the preparation of gluco-oligosaccharides fromdextran using a catalyst with both acidic and ionic groups. The catalystwas prepared according to the procedure set forth in Example 1 above.

The gluco-oligosaccharides were prepared from dextrose following theprocedure of Example 2 as described above, except that the totalreaction time was extended to 6 hours. The resulting oligosaccharideconcentrate was analyzed by HPLC to determine the product distributionover DP, the extent of formation of sugar degradation products, and thereaction mass balance closure. The product was determined to contain82.5% kg/kg DP3+ oligosaccharides, 6.9% kg/kg DP2 oligosaccharides, 9.5%kg/kg DP1 sugars, and 0.8% kg/kg total levoglucosan, levulinic acid,acetic acid, and 5-hydroxymethylfurfural.

Example 4 Preparation of Short Gluco-Galacto-Oligosaccharides (“GOSShort”)

This Example demonstrates the preparation ofgluco-galacto-oligosaccharides from lactose using a catalyst with bothacidic and ionic groups. The catalyst was prepared according to theprocedure set forth in Example 1 above.

The gluco-galacto-oligosaccharides were prepared following the procedureof Example 2 as described above, except that food-grade lactose was usedas the starting material instead of dextrose. The resultingoligosaccharide concentrate was analyzed by HPLC to determine theproduct distribution over DP, the extent of formation of sugardegradation products, and the reaction mass balance closure. The productwas determined to contain 71.8% kg/kg DP3+ oligosaccharides, 11.3% kg/kgDP2 oligosaccharides, 15.2% kg/kg DP1 sugars, and 0.8% kg/kg totallevoglucosan, levulinic acid, acetic acid, and 5-hydroxymethylfurfural.

Example 5 Preparation of Long Gluco-Galacto-Oligosaccharides (“GOSLong”)

This Example demonstrates the preparation of longgluco-galacto-oligosaccharides from lactose using a catalyst with bothacidic and ionic groups. The catalyst was prepared according to theprocedure set forth in Example 1 above.

The gluco-galacto-oligosaccharides were prepared following the procedureof Example 2 as described above, except that food-grade lactose was usedas the starting material instead of dextrose and the total reaction timewas extended to 6 hours. The resulting oligosaccharide concentrate wasanalyzed by HPLC to determine the product distribution over DP, theextent of formation of sugar degradation products, and the reaction massbalance closure. The product was determined to contain 83.2% kg/kg DP3+oligosaccharides, 5.8% kg/kg DP2 oligosaccharides, 9.0% kg/kg DP1sugars, and 0.5% kg/kg total levoglucosan, levulinic acid, acetic acid,and 5-hydroxymethylfurfural.

Example 6 Preparation of Short Manno-Oligosaccharides (“MOS Short”)

This Example demonstrates the preparation of shortmanno-oligosaccharides from mannose using a catalyst with both acidicand ionic groups. The catalyst was prepared according to the procedureset forth in Example 1 above.

A 5 L jacketed 316L stainless steel reactor (Parr Instrument Company,Moline, Ill. USA) was equipped with an anchor mixing element with aneffective diameter of approximately 95% that of the reactor cleardiameter and a vacuum condenser. The temperature of the reactor contentswas controlled by flowing pressurized hot water through the reactorjacket and measured via a thermocouple installed along the internal wallof the reactor cylinder.

The reactor was charged with 0.35 wet kg of catalyst prepared accordingto the procedure described in Example 1 above (moisture content of 44%kg/kg), 1.0 dry kg of reagent grade mannose, and 0.15 kg of de-ionizedwater. The contents were mixed at a speed of 60 rotations of the mixingelement per minute, the pressure was reduced to 50-100 Torr, and thetemperature was gradually increased to 105° C. After reaching a steadytemperature, the reactants were maintained at 105° C. and 100 Torr withmixing for a total of 4 hours.

At the completion of the reaction, approximately 5 kilograms ofdeionized water were added to the reactor and the contents mixed at 60degrees Celsius for 15 minutes to dilute the product mixture. Thereactor was drained and the resulting slurry was vacuum-filtered througha 0.45 micron polyethersulfone membrane to remove the productoligosaccharide solution from the solid catalyst. Two additionalreaction batches were performed and the resulting filtrates werecombined into a single product liquor that was concentrated toapproximately 70 Brix by vacuum rotary evaporation at 50 mTorr. Theresulting oligosaccharide concentrate was analyzed by HPLC to determinethe product distribution over DP, the extent of formation of sugardegradation products, and the reaction mass balance closure. The productwas determined to contain 42.0% kg/kg DP3+, 17.4% kg/kg DP2, 36.9% kg/kgand <0.1% kg/kg sugar caramelization products (levulinic acid, aceticacid, and levoglucosan).

Example 7 Preparation of Long Manno-Oligosaccharides (“MOS Long”)

This Example demonstrates the preparation of long manno-oligosaccharidesfrom mannose using a catalyst with both acidic and ionic groups. Thecatalyst was prepared according to the procedure set forth in Example 1above.

The manno-oligosaccharides were prepared following the procedure ofExample 6 as described above, except that the total reaction time wasextended to 6 hours. The resulting oligosaccharide concentrate wasanalyzed by HPLC to determine the product distribution over DP, theextent of formation of sugar degradation products, and the reaction massbalance closure. The product was determined to contain 65.2% kg/kg DP3+oligosaccharides, 11.7% kg/kg DP2 oligosaccharides, 20.4% kg/kg DP1sugars, and 0.5% kg/kg total levoglucosan, levulinic acid, acetic acid,and 5-hydroxymethylfurfural.

Example 8 Preparation of Xylo-Oligosaccharides (“XOS”)

This Example demonstrates the preparation of xylo-oligosaccharides fromxylose using a catalyst with both acidic and ionic groups. The catalystwas prepared according to the procedure set forth in Example 1 above.

The xylo-oligosaccharides were prepared following the procedure ofExample 6 as described above, except that xylose was used as thestarting sugar instead of mannose. The resulting oligosaccharideconcentrate was analyzed by HPLC to determine the product distributionover DP, the extent of formation of sugar degradation products, and thereaction mass balance closure. The product was determined to contain45.0% kg/kg DP3+ oligosaccharides, 23.2% kg/kg DP2 oligosaccharides,31.7% kg/kg DP1 sugars, and <0.1% kg/kg total levoglucosan, levulinicacid, acetic acid, 5-hydroxymethylfurfural, and furfural.

Example 9 Preparation of Arabino-Xylo-Oligosaccharides (“AXOS”)

This Example demonstrates the preparation ofarabino-xylo-oligosaccharides from arabinose and xylose using a catalystwith both acidic and ionic groups. The catalyst was prepared accordingto the procedure set forth in Example 1 above.

The xylo-oligosaccharides were prepared following the procedure ofExample 6 as described above, except that a 50/50 mixture of xylose andarabinose was used as the starting material instead of mannose. Theresulting oligosaccharide concentrate was analyzed by HPLC to determinethe product distribution over DP, the extent of formation of sugardegradation products, and the reaction mass balance closure. The productwas determined to contain 50.6% kg/kg DP3+ oligosaccharides, 18.0% kg/kgDP2 oligosaccharides, 31.4% kg/kg DP1 sugars, and <0.1% kg/kg totallevoglucosan, levulinic acid, acetic acid, 5-hydroxymethylfurfural, andfurfural.

Example 10 Feed Trials and Determination of Weight Gain and FeedConversion in Poultry

This Example demonstrates the effect that feeding oligosaccharidesprepared using a catalyst with both acidic and ionic groups has on theweight gain and feed conversion in poultry.

The catalyst was prepared according to the procedure set forth inExample 1 above. The oligosaccharides were prepared according to theprocedures set forth in Examples 2 through 9 above.

Nineteen groups of broiler hens were fed a diet for 35 days, prepared byblending a standard poultry feed with either one oligosaccharideprepared according to according to Example 2 through Example 9 above; acommercially-available fructo-oligosaccharide obtained from inulin; acommercially-available enzymatic feed additive (Econase® XT, AB VistaFeed Ingredients, UK); or no additive. The standard poultry feedincluded the components listed in Table 2 below. The additive identityand concentration used (inclusion rate) for each group is listed inTable 3 below.

The mass gain, ileal volatile fatty acid (VFA) content, ileal shortchain fatty acid (SCFA) content, caecal CFA content, and caecal SCFAcontent for each group of poultry was measured on days 14 and 35.

TABLE 2 Components of standard base feeds used in blending ComponentStarter (1) Grower (2) Wheat 57.37%  67.88% Soybean Meal 34.7%  27.09%Sunflower Oil  4% 1.47% Monocalcium phosphate 1.5% 1.5% Limestone 1.3%1.3% NaCl 0.4% 0.4% Mineral premix (3) 0.2% 0.2% Vitamin premix (4) 0.2%0.2% Methionine 0.24%  0.24% Lysine 0.09%  0.09% Threonine 0.0% 0.0% (1)Starter formulation used for the first two weeks (2) Grower formulationused for the following three weeks (3) Calcium 296.8 g/kg, iron 12.5g/kg, copper 4 g/kg, manganese 25 g/kg, zinc 32.5 g/kg, iodine 0.225g/kg, selenium 0.1 g/kg (4) Calcium 331.3 g/kg, vitamin A 6,000,000 ID,vitamin D3 225000 IU, vitamin E 3000, tocoferol 27270 mg/mk, vitamin K31505 mg/kg, vitamin B1 1257.3 mg/kg, vitamin B2 3000 mg/kg, vitamin B62009.7 mg/kg, vitamin B12 12.5 mg/kg, biotin 75 mg/kg, folic acid 504mg/kg, niacin 20072 mg/kg, panthotenic acid 7506.8 mg/kg

TABLE 3 Feeds additives included in diet # Inclusion Trial ReplicateRate in Diet # Oligosaccharide Feed Label Pens (wt %) 1 None Control 6 —2 GLOS Short GLOS Short 100 4 0.01% 3 GLOS Short GLOS Short 1000 5 0.1%4 GLOS Long GLOS Long 100 4 0.01% 5 GLOS Long GLOS Long 1000 5 0.1% 6GOS Short GOS Short 100 4 0.01% 7 GOS Short GOS Short 1000 5 0.1% 8 GOSLong GOS Long 100 4 0.01% 9 GOS Long GOS Long 1000 5 0.1% 10 MOS ShortMOS Short 100 4 0.01% 11 MOS Short MOS Short 1000 5 0.1% 12 MOS Long MOSLong 100 4 0.01% 13 MOS Long MOS Long 1000 5 0.1% 14 XOS XOS 100 4 0.01%15 XOS XOS 1000 5 0.1% 16 AXOS AXOS 100 4 0.01% 17 AXOS AXOS 1000 5 0.1%18 Comparative FOS 500 5 0.5% Example FOS 19 Comparative Econase 100 50.1% Example Econase

The temperature of the enclosure used for the poultry was raised to 32°C. two days before the chicks arrived. Luminosity was adjusted to 20lux. Brooder lamps were adjusted to provide extra heating to the chicksduring the first week. The temperature was gradually decreased to 22° C.over the rearing period. Temperature, ventilation and humidity weremonitored and recorded throughout the experiment on a daily basis. Thedark hours were gradually increased within a week, so that light-darkcycle was 18 hours light and 6 hours dark daily.

Newly-hatched male Ross 508 broiler chicks were randomly allocated totreatment. Each chick was marked with permanent color on the feathersthat identified the treatment but not the individual animal. Birds werehoused in 88 open pens (1.125 square meters each) with wood shavingslitter. The numbers of replicate pens for the treatments are shown inTable 3.

At the start of the trial, there were 15 birds in each pen and the totalnumber of birds was 1320. A veterinarian checked the health of thechicks at the beginning of the trial and 4 birds from one pen of thecontrol treatment had to be euthanized. The birds were observed twice aday. Chicks with compromised health were excluded from the trial. Feedand water were available ad libitum at all times.

The chicks were weighed on days 0, 14, 21 and 35. Correspondingly, feedintake per pen and the feed conversion ratio (FCR) were measured for thefollowing periods: days 0-14, starter diet period; days 14-21, earlygrower diet period; days 21-35, later grower diet period. Dead birds andbirds euthanized because of health problems were weighed. Dailymortality was recorded. FCR was calculated both corrected anduncorrected for mortality.

On day 14 two birds per pen were euthanized by cervical dislocation, theabdominal cavity opened, and the entire ileum and the paired caecaremoved for various analyses. On day 35 three birds per pen wereeuthanized and sampled in the same way as on day 14. Ileal and caecaldigesta samples were packed in individual plastic bags, and frozenimmediately for analyses. On day 35 blood samples (1.5 ml+heparin) weretaken from 2 birds per pen and frozen immediately for analysis.Cumulatively, 440 ileal, 440 caecal digesta and 176 blood samples werecollected in the trial.

Immediately after recovering the ileal digesta from a bird, the digestawas thoroughly mixed with a plastic rod, 1 gram introduced in amicrofuge tube, centrifuged at 5,000×g for 10 minutes and thesupernatant immediately measured for viscosity. At 14- and 35-day timepoints ileal digesta viscosity was measured in 2 birds from 56 pens(pens being fed with diets 1, 3, 5, 7, 9, 11, 13, 15, 17, 18 and 19),with 224 measurements taken in total (2 time points×56 pens×2 birds).

The lactic acid and volatile fatty acid (“VFA”) content were analysed bygas chromatography using a packed column for the analysis of free acids.The short-chain fatty acids (SCFAs) quantified were acetic, propionic,butyric, iso-butyric, 2-methyl-butyric, valeric, iso-valeric and lacticacid. SCFAs were analysed in ileal and caecal digesta of two birds perpen at both sampling points. Thus SCFAs were analysed in 352 ileal and352 caecal digesta samples, with 704 samples analysed in total (2 timepoints×88 pens×2 birds).

Performance data was analysed by Dunnett's (2-sided) test using JMPstatistical software package (version 12 EA). Results of the SCFAanalysis were analysed by independent samples T-test. In all tests, thetreatment group 1 (unamended diet) was used as a control against whichthe test treatments were compared.

The mean weight gain in grams of each group after the first 14 days isshown in FIG. 13 . The upper decision limit (UDP) and lower decisionlimit (LDP) using a threshold of 0.05 are depicted.

The mean weight gain in grams of each group at the end of the 35 dayperiod is shown in FIG. 14 . The upper decision limit (UDP) and lowerdecision limit (LDP) using a threshold of 0.05 are depicted.

The feed conversion ratio (FCR) for each group at the end of the 35 dayperiod, corrected for mortality, is shown in FIG. 15 .

The total SCFA concentration in the caecum from a sample of birds ineach group at the end of 35 days is shown in FIG. 16 .

The butyric acid concentration in the caecum from a sample of birds ineach group at the end of 35 days is shown in FIG. 17 .

The mean weight gain of each group at the end of the 35 day period isshown in FIG. 14 . All treatments resulted in heavier birds relative tothe control (control gain=2175.83 g). It was unexpectedly observed thatseveral of the oligosaccharide additives, in particular “GLOS Long”(prepared as in Example 3), “GOS Short” (prepared as in Example 4), “GOSLong” (prepared as in Example 5), “MOS Short” (prepared as in Example6), and “MOS Long” (prepared as in Example 7), provided a statisticallysignificant (p<0.05, Dunnetts) increase in poultry weight at the lowinclusion rate of 0.01%, as compared to the control (no additive).

The oligosaccharide additives “AXOS” (prepared as in Example 9), “GOSShort” (prepared as in Example 2), and “XOS” (prepared as in Example 8)did not result in a statistically significant increase in poultry weightat the inclusion rate of 0.01%, as compared to the control. In contrast,the commercial prebiotic FOS failed to provide a statisticallysignificant increase in weight even at the inclusion rate of 0.05%,which is up to five times the inclusion rate of the oligosaccharideadditives.

The feed conversion ratio (FCR) was decreased for most groups fedadditives, compared to the control (control mean FCR=1.625). The groupfed “AXOS” (prepared as in Example 9) exhibited a statisticallysignificant reduction in FCR at the inclusion rate of 0.1%.

The presence of the various oligosaccharide additives did not result inany significant change to the ileal digesta viscosity of the birds at 35days relative to the control, as shown in Table 4.

TABLE 4 Ileal digesta viscosity of at the end of 35 day period Trial #Treatment Viscosity 1 Control 6.0 3 GLOS L-DP 1000 5.8 5 GLOS H-DP 10007.4 7 XOS 1000 6.4 9 MOS L-DP 1000 5.8 11 MOS H-DP 1000 6.3 13 AXOS 10006.3 15 GOS L-DP 1000 6.8 17 GOS H-DP 1000 7.3 18 FOS 500 7.5 19 Econase100 4.8

Compared to the control, the concentrations of caecal SCFA increased forgroups fed a diet including an oligosaccharide additive. In particular,the group fed “GLOS Long” (prepared as in Example 3) showed a caecalbutyric acid concentration of 21.5 mM at an inclusion rate of 0.01%, asshown in FIG. 17 .

These results indicate that including oligosaccharide additives preparedusing a catalyst with both acidic and ionic moieties in poultry feedeffectively increases the weight gain of poultry.

Example 11 Preparation and Purification of Gluco-Oligosaccharides

This Example demonstrates the preparation and purification ofgluco-oligosaccharides from food grade dextrose using a catalyst withboth acidic and ionic groups. The catalyst was prepared according to theprocedure set forth in Example 1 above.

The gluco-oligosaccharides were prepared from dextrose following theprocedure of Example 2 as described above, except as follows. The DP3+content of the product mixture was monitored by HPLC, and the reactionwas stopped when the DP3+ content reached 73%±2% dry kg DP3+oligosaccharides per dry kilogram of solids. Following recovery from thereactor, the syrup was filtered through a 0.2 micron ceramic membranefilter (Pall Corporation, Westborough, Mass. USA) using a backpressureof 30-60 psi. The permeate was then run sequentially through a 3 literpacked bed of Dowex Monosphere 88 strong acid cationic exchange resin, a3 liter bed of Dowex Monosphere 66 weak base anionic exchange resin, anda 3 liter bed of Dowex Optipore-SD-2 absorbant resin, resulting in apale-yellow syrup with neutral pH and minimal odor. The syrup was thenconcentrated to a final solids content of 65% kg dry solids per kg ofsyrup using a horizontal wiped-film vacuum evaporator.

The resulting concentrated gluco-oligosaccharide syrup was determined byHPLC and conductivity to contain less than 1 ppm total formic acid,levulinic acid, and 5-hydroxymethylfurfural. Bacterial analysisconfirmed a total aerobic plate count <10 cfu/g, Escherichia coli <10cfu/g, Staphylococcus aureus <10 cfu/g, total coliform <10 cfu/g, andthat the syrup was negative for Salmonella spp, under the methods of theUS FDA Bacterial Analytical Manual (BAM), Edition 8, Rev. A, 1998. Theresulting concentrated gluco-oligosaccharide syrup was determined byICP-MS to contain less than 10 ppb arsenic, less than 10 ppb cadmium,less than 10 ppb lead, less than 10 ppb mercury, less than 0.2 ppmnickel, and 1.2 ppm zinc.

The distribution over glycosidic bond types in the gluco-oligosaccharidemixture was determined by 2D-JRES NMR to be: 11±1 mol % α-(1,2)glycosidic linkages, 35±4 mol % β-(1,2) glycosidic linkages, 6±1 mol %α-(1,3) glycosidic linkages, 3±1 mol % β-(1,3) glycosidic linkages,1±0.5 mol % α-(1,4) glycosidic linkages, 21±2 mol % β-(1,4) glycosidiclinkages, 15±2 mol % α-(1,6) glycosidic linkages, and 8±1 mol % β-(1,6)glycosidic linkages.

Example 12 Preparation and Purification ofGluco-Galacto-Oligosaccharides

This Example demonstrates the preparation and purification ofgluco-galacto-oligosaccharides from food grade lactose using a catalystwith both acidic and ionic groups. The catalyst was prepared accordingto the procedure set forth in Example 1 above.

The gluco-galacto-oligosaccharides were prepared from lactose followingthe procedure of Example 4 as described above, except as follows. Thetotal reaction time was adjusted to yield a reaction product with a DP3+content of 73%±2% dry kg DP3+ oligosaccharides per dry kilogram ofsolids, as determined by HPLC. Following recovery from the reactor, thesyrup was filtered through a 0.2 micron ceramic membrane filter (PallCorporation, Westborough, Mass. USA) using a backpressure of 30-60 psi.The permeate was then run sequentially through a 3 liter packed bed ofDowex Monosphere 88 strong acid cationic exchange resin, a 3 liter bedof Dowex Monosphere 66 weak base anionic exchange resin, and a 3 literbed of Dowex Optipore-SD-2 absorbant resin, resulting in a pale-yellowsyrup with neutral pH and minimal odor. The syrup was then concentratedto a final solids content of 65% kg dry solids per kg of syrup using ahorizontal wiped-film vacuum evaporator.

The resulting concentrated gluco-galacto-oligosaccharide syrup wasdetermined by HPLC and conductivity to contain less than 1 ppm totalformic acid, levulinic acid, and 5-hydroxymethylfurfural. Bacterialanalysis confirmed a total aerobic plate count <10 cfu/g, Escherichiacoli <10 cfu/g, Staphylococcus aureus <10 cfu/g, total coliform <10cfu/g, and that the syrup was negative for Salmonella spp, under themethods of the US FDA Bacterial Analytical Manual (BAM), Edition 8, Rev.A, 1998. The resulting concentrated gluco-oligosaccharide syrup wasdetermined by ICP-MS to contain less than 10 ppb arsenic, less than 10ppb cadmium, less than 10 ppb lead, less than 10 ppb mercury, less than0.2 ppm nickel, and 0.520 ppm zinc.

The distribution over glycosidic bond types in the gluco-oligosaccharidemixture was determined by proton and JRES NMR to be: between 0-10 mol %α-(1,2) glycosidic linkages, between 0-10 mol % β-(1,2) glycosidiclinkages, between 5-15 mol % α-(1,3) glycosidic linkages, between 2-10mol % β-(1,3) glycosidic linkages, between 2-15 mol % α-(1,4) glycosidiclinkages, between 10-50 mol % β-(1,4) glycosidic linkages, between 5-25mol % α-(1,6) glycosidic linkages, and between 20-50 mol % β-(1,6)glycosidic linkages.

Example 13 Preparation of a Gluco-Oligosaccharide Pre-Mix

The gluco-oligosaccharide from Example 11 was combined with milled cornmeal as a carrier material in a ratio of approximately 1 kggluco-oligosaccharide syrup to 4 kg of corn meal. The resulting mixturewas blended to achieve a uniform distribution of gluco-oligosaccharides,producing a dry, flowable power with a moisture content below 12% kg/kg

Example 14 Preparation of Gluco-Oligosaccharide Pre-Mixes

The procedure of Example 13 was repeated for each of following carriers,used in place of milled corn: ground rice hulls, feed grade silica gel,feed grade fumed silica, corn gluten feed, corn gluten meal, and drieddistiller's grains. Where necessary, the blended material was dried to amaximum final moisture content of 10 wt %.

Example 15 Preparation of a Gluco-Galacto-Oligosaccharide Pre-Mix

The gluco-galacto-oligosaccharide from Example 12 was combined withmilled corn meal as a carrier material in a ratio of approximately 1 kggluco-galacto-oligosaccharide syrup to 4 kg of corn meal. The resultingmixture was blended to achieve a uniform distribution ofgluco-oligosaccharides, producing a dry, flowable power with a moisturecontent below 12% kg/kg.

Example 16 Preparation of Gluco-Galacto-Oligosaccharide Pre-Mixes

The procedure of Example 15 was repeated for each of the followingcarriers, used in place of milled corn: ground rice hulls, feed gradesilica gel, feed grade fumed silica, corn gluten feed, corn gluten meal,and dried distiller's grains. Where necessary, the blended material wasdried to a maximum final moisture content of 10 wt %

Example 17 Preparation and Purification of Gluco-Oligosaccharides

This Example demonstrates the rapid preparation and purification ofgluco-oligosaccharides from food grade dextrose using a catalyst withboth acidic and ionic groups. The catalyst was prepared according to theprocedure set forth in Example 1 above.

The gluco-oligosaccharides were prepared from dextrose following theprocedure of Example 2 as described above, except as follows. Thereaction temperature was increased to 140-160 degrees C. and thereaction time was reduced to 60-90 minutes. Following recovery from thereactor and removal of the catalyst, the product syrup was neutralizedto a pH between 5.0 and 6.5 with aqueoue sodium hydroxide solution andthen filtered through a series of 20, 10, 5, 1 and 0.2 micron inlinecartridge filters. The filtered syrup was then concentrated to a finalsolids content of 65% kg dry solids per kg of syrup using a horizontalwiped-film vacuum evaporator.

The resulting concentrated gluco-oligosaccharide syrup was determined byHPLC to have a DP3+ content of 73%±2% dry kg DP3+ oligosaccharides perdry kilogram of solids. The distribution over glycosidic bond types inthe gluco-oligosaccharide mixture was determined by 2D-JRES NMR to be:15±1 mol % α-(1,2) glycosidic linkages, 27±4 mol % β-(1,2) glycosidiclinkages, 8±1 mol % α-(1,3) glycosidic linkages, 5±1 mol % β-(1,3)glycosidic linkages, 1±0.5 mol % α-(1,4) glycosidic linkages, 20±2 mol %β-(1,4) glycosidic linkages, 11±2 mol % α-(1,6) glycosidic linkages, and15±1 mol % β-(1,6) glycosidic linkages.

Example 18 Scaled-Up Production of a Gluco-Oligosaccharide Pre-Mix

50.9 kg of the gluco-oligosaccharide from Example 17 was blended inbatches with 95.2 kg of milled corn meal using a bowl-mixer with anoverhead orbital mixer equipped with a dough-blending element. Theresulting 146.1 kg of wet pre-mix were dried in 13 kg batches using arotating drum drier with a rotation rate of approximately 60 rpm and anair flow rate of approximately 1,000 cubic feet per minute. 127.0 kg ofdried pre-mix were recovered. The moisture content was determined to bebelow 15 wt %.

Example 19 Preparation of Basal Corn-Soy Poultry Feeds

Complete corn-soy starter, grower, and finisher poultry feeds, typicalof those used in the U.S. broiler industry, were produced by blendingingredients in the following proportions:

Ingredient (lbs, as received) Starter Grower Finisher Corn 638.61 689.22747.31 Soybean meal 275.21 221.09 167.42 Animal by-product blend 50.2850.27 50.28 Dicalcium phosphate 10.56 11.06 8.65 Limestone 5.13 5.334.73 Poultry Fat 5.03 8.85 7.44 L-Lysine 4.32 3.92 3.82 Salt 3.52 3.524.02 DL-Methionine 3.22 2.71 2.31 Vitamin and Mineral Premix 2.51 2.512.51 L-Threonine 0.90 0.80 0.80 Bacitracin 0.00 0.00 0.00 Saccox 0.500.50 0.50 Enzyme blend 0.20 0.20 0.20 Total 1000.00 1000.00 1000.00

The nutritional properties of the feeds were calculated to be:

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy 1381 1413 1437 (cal/lb) Crude protein, wt % 22.11 19.96 17.92Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.70 0.63 0.56Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.92 0.82 0.73Calcium, wt % 0.90 0.90 0.80 Available P, wt % 0.45 0.45 0.40 Sodium, wt% 0.20 0.20 0.22

The feeds contained an ionophore anti-coccidial and an enzyme blendcomprising a phytase and non-starch polysaccharide carbohydratases(NSPases). Raw ingredients were formed into peletized poultry feed asfollows. The raw ingredients were combined in a ribbon blender, afterwhich they were conveyed to a 160-180 degree F. steam-injectedconditioner. The conditioned feed was pressed through a rotating-dyepeletizer to produce hot pellets, which were then cooled in a fluidizedair cooler. The resulting feed pellets were metered into 50 pound lined,multi-wall paper bags, which were sealed until use. The starter feedpellets were crumbled prior to bagging.

Example 20 Preparation of Basal Corn-Soy Poultry Feeds

Complete corn-soy starter, grower, and finisher poultry feeds, typicalthose used in the U.S. broiler industry, were produced by blendingingredients as follows:

Ingredient (lbs, as received) Starter Grower Finisher Corn 1187.361281.44 1400.68 Soybean meal 714.71 619.51 516.94 Bone meal 40.00 40.0020.00 Limestone 23.24 22.73 22.97 Phosphate (defluorinated) 7.83 3.896.60 Salt 7.63 8.13 8.29 DL-Methionine 7.14 6.11 5.47 Threonine 2.281.75 1.82 L-Lysine 2.25 1.75 2.45 Vitamin and Mineral Premix 4.00 4.004.00 Soy oil 1.42 8.55 9.48 Salinomycin 0.84 0.84 0.00 Choline 0.80 0.800.80 Enzyme blend 0.50 0.50 0.50 Total 2000.00 2000.00 2000.00

The nutritional content of the feed based on the ingredient inclusionswas calculated to be:

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy 1379 1412 1436 (cal/lb) Crude protein, wt % 22.10 20.84 18.33Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.69 0.61 0.55Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.918 0.82 0.733Calcium, wt % 0.965 0.88 0.82 Available P, wt % 0.47 0.43 0.40 Sodium,wt % 0.21 0.21 0.21

The starter and grower feeds contained an ionophore anti-coccidial andan enzyme blend comprising a phytase and a mixture of non-starchpolysaccharide carbohydratases (NSPases), while the finisher feedcontained the enzyme blend but not the ionophore. Raw ingredients wereformed into peletized poultry feed as follows. The raw ingredients werecombined in a ribbon blender, after which they were conveyed to asteam-injected conditioner. The conditioned feed was pressed through arotating-dye peletizer to produce hot pellets, which were then cooled ina fluidized air cooler. The starter feed pellets were crumbled, and theresulting feeds were metered into bulk storage bins until use.

Example 21 (Comparative Example 1) Preparation of Feeds ContainingAntibiotic Growth Promoters

Complete starter, grower, and finisher feeds were produced according tothe procedure of Example 19, except that bacitracin (BMD®-50, Zoetis)was added on top of the basal diet, resulting in diets with thefollowing compositions:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 638.29688.88 746.93 Soybean meal 275.08 220.98 167.34 Animal by-product blend50.25 50.25 50.25 Dicalcium phosphate 10.55 11.05 8.64 Limestone 5.135.33 4.72 Poultry Fat 5.03 8.84 7.44 L-Lysine 4.32 3.92 3.82 Salt 3.523.52 4.02 DL-Methionine 3.22 2.71 2.31 Vitamin and Mineral Premix 2.512.51 2.51 L-Threonine 0.90 0.80 0.80 Bacitracin 0.50 0.50 0.50 Saccox0.50 0.50 0.50 Enzyme blend 0.20 0.20 0.20 Total 1000.00 1000.00 1000.00

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy (cal/lb) 1380 1412 1436 Crude protein, wt % 22.10 19.95 17.91Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.70 0.63 0.56Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.92 0.82 0.73Calcium, wt % 0.90 0.90 0.80 Available P, wt % 0.45 0.45 0.40 Sodium, wt% 0.20 0.20 0.22

Example 22 (Comparative Example 2) Preparation of Feeds ContainingSoluble Corn Fiber

Complete starter, grower, and finisher feeds were produced according tothe procedure of Example 20, except that soluble corn fiber(Fibersol®-LQ, Acher Daniels Midland Company, USA) was added on top ofthe basal diet. The distribution over glycosidic bond types in thesoluble corn fiber was determined by 2D-JRES NMR to be: <10 mol %α-(1,2) glycosidic linkages, ≤9 mol % β-(1,2) glycosidic linkages, ≤9mol % α-(1,3) glycosidic linkages, ≥16 mol % β-(1,3) glycosidiclinkages, ≥9 mol % α-(1,4) glycosidic linkages, ≤15% mol % β-(1,4)glycosidic linkages, ≥19 mol % α-(1,6) glycosidic linkages, and ≤12 mol% β-(1,6) glycosidic linkages. Diets were prepared by adding the solublecorn fiber at an inclusion rate of 625 ppm (dry solids basis per totalfinal feed), resulting in the following compositions:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 1186.611280.64 1399.81 Soybean meal 714.27 619.12 516.62 Animal by-productblend 39.98 39.98 19.99 Dicalcium phosphate 23.23 22.72 22.96 Limestone7.83 3.89 6.60 Poultry Fat 7.63 8.12 8.28 L-Lysine 7.14 6.11 5.47 Salt2.28 1.75 1.82 DL-Methionine 2.25 1.75 2.45 Vitamin and Mineral Premix4.00 4.00 4.00 L-Threonine 1.42 8.54 9.47 Soluble Corn Fiber 0.84 0.840.00 Saccox 0.80 0.80 0.80 Enzyme blend 1.25 1.25 1.25 Total 0.50 0.500.50 2000.00 2000.00 2000.00

Example 23 (Comparative Example 3) Preparation of Feeds ContainingSoluble Wheat Fiber

Complete starter, grower, and finisher feeds were produced according tothe procedure of Example 20, except that soluble wheat fiber (PremiDex™,modified wheat starch, Acher Daniels Midland Company, USA) was added ontop of the basal diet at an inclusion rate of 714 ppm (dry solids basisper total final feed), resulting in diets with the followingcompositions:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 1186.511280.53 1399.68 Soybean meal 714.20 619.07 516.57 Animal by-productblend 39.97 39.97 19.99 Dicalcium phosphate 23.22 22.71 22.95 Limestone7.82 3.89 6.60 Poultry Fat 7.62 8.12 8.28 L-Lysine 7.13 6.11 5.47 Salt2.28 1.75 1.82 DL-Methionine 2.25 1.75 2.45 Vitamin and Mineral Premix4.00 4.00 4.00 L-Threonine 1.42 8.54 9.47 Modified Wheat Starch 0.840.84 0.00 Saccox 0.80 0.80 0.80 Enzyme blend 1.43 1.43 1.43 Total 0.500.50 0.50 2000.00 2000.00 2000.00

Example 24 (Comparative Example 4) Preparation of Feeds Containing YeastMannans

Complete starter, grower, and finisher feeds were produced according tothe procedure of Example 20, except that yeast cell-wall mannan(CitriStim®, Archer Daniels Midland Company, USA) was added on top ofthe basal diet at an inclusion rate of 2,273 ppm (dry solids basis pertotal final feed), resulting in diets with the following compositions:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 1184.661278.53 1397.50 Soybean meal 713.09 618.11 515.77 Animal by-productblend 39.91 39.91 19.95 Dicalcium phosphate 23.19 22.68 22.92 Limestone7.81 3.88 6.59 Poultry Fat 7.61 8.11 8.27 L-Lysine 7.12 6.10 5.46 Salt2.27 1.75 1.82 DL-Methionine 2.24 1.75 2.44 Vitamin and Mineral Premix3.99 3.99 3.99 L-Threonine 1.42 8.53 9.46 Yeast Mannan 0.84 0.84 0.00Saccox 0.80 0.80 0.80 Enzyme blend 4.54 4.54 4.54 Total 0.50 0.50 0.502000.00 2000.00 2000.00

Example 25 (Comparative Example 5) Preparation of Feeds ContainingXylo-Oligosaccharides

Complete starter, grower, and finisher feeds were produced according tothe procedure of Example 20, except that xylo-oligosaccharide(X35P™,LongLive, China) was added on top of the basal diet at an inclusion rateof 1,429 ppm (dry solids basis per total final feed), resulting in dietswith the following compositions:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 1185.661279.61 1398.68 Soybean meal 713.69 618.63 516.20 Animal by-productblend 39.94 39.94 19.97 Dicalcium phosphate 23.21 22.70 22.94 Limestone7.82 3.88 6.59 Poultry Fat 7.62 8.12 8.28 L-Lysine 7.13 6.10 5.46 Salt2.28 1.75 1.82 DL-Methionine 2.25 1.75 2.45 Vitamin and Mineral Premix3.99 3.99 3.99 L-Threonine 1.42 8.54 9.47 xylo-oligosaccharide 0.84 0.840.00 Saccox 0.80 0.80 0.80 Enzyme blend 2.85 2.85 2.85 Total 0.50 0.500.50 2000.00 2000.00 2000.00

Example 26 Preparation of Finished Poultry Feeds ContainingGluco-Oligosaccharides

Complete starter, grower, and finisher corn-soy poultry feeds wereprepared following the procedure of Example 19, except that thegluco-oligosaccharide from Example 11 (provided in the form of thepremix of Example 13) was added on top of the diets to prepare finalfeeds with 50±5, 100±5, 250±5, and 500±5 ppm inclusion rates.

Example 26.1

The 50 ppm gluco-oligosaccharide diet was prepared as follows:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 638.58689.19 747.27 Soybean meal 275.20 221.08 167.41 Animal by-product blend50.27 50.27 50.27 Dicalcium phosphate 10.56 11.06 8.65 Limestone 5.135.33 4.73 Poultry Fat 5.03 8.85 7.44 L-Lysine 4.32 3.92 3.82 Salt 3.523.52 4.02 DL-Methionine 3.22 2.71 2.31 Vitamin and Mineral Premix 2.512.51 2.51 L-Threonine 0.90 0.80 0.80 Gluco-oligosaccharide 0.05 0.050.05 Saccox 0.50 0.50 0.50 Enzyme blend 0.20 0.20 0.20 Total 1000.001000.00 1000.00

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy (cal/lb) 1381 1413 1437 Crude protein, wt % 22.11 19.96 17.92Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.70 0.63 0.56Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.92 0.82 0.73Calcium, wt % 0.90 0.90 0.80 Available P, wt % 0.45 0.45 0.40 Sodium, wt% 0.20 0.20 0.22

Example 26.2

The 100 ppm gluco-oligosaccharide diet was prepared as follows:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 638.58689.19 747.27 Soybean meal 275.20 221.08 167.41 Animal by-product blend50.27 50.27 50.27 Dicalcium phosphate 10.56 11.06 8.65 Limestone 5.135.33 4.73 Poultry Fat 5.03 8.85 7.44 L-Lysine 4.32 3.92 3.82 Salt 3.523.52 4.02 DL-Methionine 3.22 2.71 2.31 Vitamin and Mineral Premix 2.512.51 2.51 L-Threonine 0.90 0.80 0.80 Gluco-oligosaccharide 0.10 0.100.10 Saccox 0.50 0.50 0.50 Enzyme blend 0.20 0.20 0.20 Total 1000.001000.00 1000.00

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy (cal/lb) 1380 1412 1436 Crude protein, wt % 22.10 19.95 17.91Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.70 0.63 0.56Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.92 0.82 0.73Calcium, wt % 0.90 0.90 0.80 Available P, wt % 0.45 0.45 0.40 Sodium, wt% 0.20 0.20 0.22

Example 26.3

The 250 ppm gluco-oligosaccharide diet was prepared as follows:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 638.58689.19 747.27 Soybean meal 275.20 221.08 167.41 Animal by-product blend50.27 50.27 50.27 Dicalcium phosphate 10.56 11.06 8.65 Limestone 5.135.33 4.73 Poultry Fat 5.03 8.85 7.44 L-Lysine 4.32 3.92 3.82 Salt 3.523.52 4.02 DL-Methionine 3.22 2.71 2.31 Vitamin and Mineral Premix 2.512.51 2.51 L-Threonine 0.90 0.80 0.80 Gluco-oligosaccharide 0.25 0.250.25 Saccox 0.50 0.50 0.50 Enzyme blend 0.20 0.20 0.20 Total 1000.001000.00 1000.00

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy (cal/lb) 1380 1412 1436 Crude protein, wt % 22.10 19.95 17.91Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.70 0.63 0.56Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.92 0.82 0.73Calcium, wt % 0.90 0.90 0.80 Available P, wt % 0.45 0.45 0.40 Sodium, wt% 0.20 0.20 0.22

Example 26.4

The 500 ppm gluco-oligosaccharide diet was prepared as follows:

Ingredient (lbs, dry solids basis) Starter Grower Finisher Corn 638.58689.19 747.27 Soybean meal 275.20 221.08 167.41 Animal by-product blend50.27 50.27 50.27 Dicalcium phosphate 10.56 11.06 8.65 Limestone 5.135.33 4.73 Poultry Fat 5.03 8.85 7.44 L-Lysine 4.32 3.92 3.82 Salt 3.523.52 4.02 DL-Methionine 3.22 2.71 2.31 Vitamin and Mineral Premix 2.512.51 2.51 L-Threonine 0.90 0.80 0.80 Gluco-oligosaccharide 0.50 0.500.50 Saccox 0.50 0.50 0.50 Enzyme blend 0.20 0.20 0.20 Total 1000.001000.00 1000.00

Nutritional Property Starter Grower Finisher Apparent metabolizableenergy (cal/lb) 1379 1411 1435 Crude protein, wt % 22.09 19.94 17.90Total Lys, wt % 1.35 1.20 1.06 Total Methionine, wt % 0.70 0.63 0.56Total TSAA, wt % 1.02 0.92 0.83 Total Threonine, wt % 0.92 0.82 0.73Calcium, wt % 0.90 0.90 0.80 Available P, wt % 0.45 0.45 0.40 Sodium, wt% 0.20 0.20 0.22

Example 27 Preparation of Finished Poultry Feeds ContainingGluco-Galacto-Oligosaccharides

Complete starter, grower, and finisher corn-soy poultry feeds wereprepared following the procedure of Example 26, except that thegluco-galacto-oligosaccharide from Example 12 (provided as the premix ofExample 15) was used in place of gluco-oligosaccharide. The resultingfeeds contained 50±5 (Example 27.1), 100±5 (Example 27.2), 250±5 Example27.3), and 500±5 (Example 27.3) ppm of gluco-galacto-oligosaccharide,respectively.

Example 28 Demonstration of Live Performance Benefits at Low InclusionRate

Newly hatched straight-run Cobb 500 broiler chickens, vaccinated forMarek's and Newcastle Disease, were placed on built-up litter in floorpens with a packing density typical of the U.S. broiler industry. Waterwas provided ad libitum throughout the study via nipple drinkers. Feedwas provided ad libitum throughout the study via one hanging overheadfeeder per pen. Feed added and removed from pens from day 0 to study endwas weighed and recorded. Lighting was provided by incandescent lightsfollowing a standard commercial program. The test facility, pens andbirds were observed at least twice daily for general flock condition,lighting, water, feed, ventilation and unanticipated events.

Starter diets were fed from Day 1 until Day 14. Grower diets were fedfrom Day 14 until Day 28. Finisher diets were fed from Day 28 until Day35. At the end of each phase, all birds and feed were weighed todetermine body weight (BW), body weight gain (BWG), feed consumption(FC), and feed conversion ratio (FCR). Mortality was recorded andweighed daily and feed conversion was corrected to a common final weightand adjusted for mortality (cFCR). The mean 0-35d BWG and 0-35d cFCR foreach treatment was determined by averaging the BWG and cFCR over penscorresponding to the same treatment. The standard deviation for eachtreatment across pens was determined accordingly.

Each dietary treatment was fed to 6 replicate pens randomized throughoutthe building as follows:

Inclusion Rate Treatment Treatment Description (dry solids basis) 1Basal Diet (Example 19) n/a 2 Antibiotic Positive Control as labeled(Comparative Example 1) 3 gluco-oligosaccharide (Example 26.1)  50 ppm 4gluco-oligosaccharide (Example 26.2) 100 ppm 5 gluco-oligosaccharide(Example 26.3) 250 ppm 6 gluco-oligosaccharide (Example 26.4) 500 ppm

The BWG Benefit for a given treatment with respect to (w.r.t.) the basaldiet (negative control) was calculated as the mean 0-35d BWG for thetreated diet divided by the mean 0-35d BWG for the basal diet, minusone. The cFCR Benefit for a given treatment w.r.t. the basal diet wascalculated as one minus the mean 0-35d cFCR for the treated diet dividedby the mean 0-35d cFCR for the basal diet.

Mean 0-35 day body weight gains (BWG) were determined to be:

Inclusion 0-35 day Benefit Rate BWG w.r.t Basal Diet Description (ppm)(g) Diet Basal Diet (Example 19) n/a 1,983 ± 11 0.0% Antibiotic PositiveControl As labeled 1,999 ± 21 0.8% (Comparative Example 1)gluco-oligosaccharide 50 2,002 ± 33 1.0% (Example 26.1)gluco-oligosaccharide 100 1,968 ± 35 −0.7% (Example 26.2)gluco-oligosaccharide 250 2,016 ± 24 1.7% (Example 26.3)gluco-oligosaccharide 500 2,054 ± 29 3.6% (Example 26.4)

Mean 0-35 day corrected feed conversion ratios (cFCR) were determined tobe:

Inclusion 0-35 d Benefit Rate cFCR w.r.t Basal Diet Description (ppm)(kg/kg) Diet Basal Diet (Example 19) n/a 1.612 ± 0.047 0.0% AntibioticPositive Control as 1.582 ± 0.025 1.9% (Comparative Example 1) labeledgluco-oligosaccharide 50 1.598 ± 0.039 0.8% (Example 26.1)gluco-oligosaccharide 100 1.596 ± 0.023 1.0% (Example 26.2)gluco-oligosaccharide 250 1.582 ± 0.033 1.8% (Example 26.3)gluco-oligosaccharide 500 1.532 ± 0.032 4.9% (Example 26.4)

The mean cFCR as a function of gluco-oligosaccharide inclusion rate isdepicted in FIG. 18 . For 500 ppm gluco-oligosaccahride, the observedcFCR of 1.532 reflects a statistically significant (p<0.02, asdetermined by two-factor ANOVA, accounting for the pen blockingstructure) benefit of 4.9% with respect to the negative control 0-35 daycFCR of 1.612, whereas the antibiotic provided only a 1.9% benefit.Similarly, the observed a 0-35 day BWG of 2.054 kg reflects astatistically significant (p<0.05, as determined by two-factor ANOVA,accounting for the pen blocking structure) benefit of 3.6% with respectto the negative control BWG of 1.983 kg, whereas the antibiotic providedonly a 0.8% benefit.

The 0-35 day mortality rate for birds fed the basal diet of Example 19was determined to be 1.7%, on a per head basis. The average 0-35 daymortality rate for birds fed diets containing the gluco-oligosaccharideof Example 11 was 0.8%, on a per head basis. Diet compositionscontaining the gluco-oligosaccharide of Example 11 therefore provide a51% reduction in the 0-35 day mortality rate with respect to the basalfeed.

Example 29 Processing of Birds

After an overnight fast, 4 birds from each of the pens in Example 28were tagged, weighed and processed as follows: birds were electricallystunned, and mechanically eviscerated. Hot carcass weight and abdominalfat pad were determined. Carcasses were then split into front and backhalves and the front halves were chilled in an ice bath for 4 hours.Front halves were then deboned to determine pectoralis major (fillet)and pectoralis minor (tender) weights.

Example 30 Limited Benefit of Other Carbohydrate Feed Ingredients(Comparative Examples)

Male Cobb 500 broiler chickens were obtained from a hatchery and placedin 3×5 ft concrete floor pens containing used wood shavings. Birds werevaccinated for Mareks at the hatchery and vaccinated for Newcastle andInfectious Bronchitis by spray application on on study Day 0. Water wasprovided ad libitum throughout the study via nipple drinkers, which werechecked twice daily and cleansed as needed to ensure a constant andclean water supply to the birds. Feed was provided ad libitum throughoutthe study via one hanging, ˜17-inch diameter tube feeder per pen. Achick feeder tray was placed in each pen for approximately the first 4days. Feed added and removed from pens from day 0 to study end wasweighed and recorded. Lighting was provided by incandescent lightsfollowing a standard commercial program. The test facility, pens andbirds were observed at least twice daily for general flock condition,lighting, water, feed, ventilation and unanticipated events.

Any mortalities or birds sacrificed for culling and/or sampling wereweighed and necropsied. Starter diets were fed from Day 1 until Day 14.Grower diets were fed from Day 14 until Day 28. Finisher diets were fedfrom Day 28 until Day 35. At the end of each phase, all birds and feedwere weighed to determine body weight (BW), body weight gain (BWG), feedconsumption (FC), and feed conversion ratio (FCR). Mortality wasrecorded and weighed daily and feed conversion was corrected to a commonfinal weight and adjusted for mortality (cFCR). The mean 0-35d BWG and0-35d cFCR for each treatment was determined by averaging the BWG andcFCR over pens corresponding to the same treatment. The standarddeviation for each treatment across pens was determined accordingly.

The BWG Benefit for a given treatment with respect to (w.r.t.) the basaldiet (negative control) was calculated as the mean 0-35d BWG for thetreated diet divided by the mean 0-35d BWG for the basal diet, minusone. The FCR Benefit for a given treatment w.r.t. the basal diet wascalculated as one minus the mean 0-35d FCR for the treated diet dividedby the mean 0-35d FCR for the basal diet.

The BWG Benefits and FCR Benefits were determined to be:

Inclusion BWG Benefit FCR Benefit Rate w.r.t Basal w.r.t Basal DietDescription (ppm) Diet Diet Soluble Corn Fiber 625 −0.1% 0.2%(Comparative Example 2) Modified Wheat Starch 714 −2.3% −0.3%(Comparative Example 3) Yeast Mannan 2273 1.2% 0.4% (Comparative Example4) Xylo-oligosaccharides 1429 0.2% 0.3% (Comparative Example 5)

The largest benefit observed for the Comparative Examples was a 1.2% BWGbenefit for Yeast Mannan (Comparative Example 4) at the high dose of2,273 ppm. In particular, Modified Wheat Starch had a negative effect onBWG and FCR.

Example 31 Reduction of Variability of Final Body Weight

The procedure of Example 10 was repeated, except that the treatedstarter, grower, and finisher diets contained 50 ppm of thegluco-oligosaccharide of Example 11. The mean 35 day body weight (BW)across pens fed the basal diet was 2,310 grams with a standard deviationof 90 grams. The relative variability in final BW (standard deviationdivided by the mean) was therefore 3.9%. Fort the diets containing 50ppm of the gluco-oligosaccharide from Example 11, the mean 0-35 day BWGwas determined to be 2,428 grams, with a standard deviation of 59 grams.The relative variability in final BW for the diet comprising thegluco-oligosaccharide from Example 11 was therefore, 2.4%. Thisrepresents a 38% reduction in the relative variability of final birdweight.

Example 32 Growth Performance Study in Necrotic Enteritis ChallengeModel in Broiler Chickens

This study evaluates the impact of gluco-oligosaccharides preparedaccording to the protocols described in the Examples above (e.g.,Example 11), in a necrotic enteritis challenge model in broilerchickens. The effects of dietary supplementation ofgluco-oligosaccharides with and without an alternative feeding programin a necrotic enteritis challenge model is evaluated.

The schedule of events for this study is performed as set forth in Table5 below.

TABLE 5 Schedule of events Activity Study Day Assign newly hatched malebroiler chicks to specific 0 treatment pens (15 chicks/pen) Weigh birds(pen basis) and weigh back feed. Raise 15 the feeder in each pen in theAM (no access to feed). Feed with challenge material after approximately8 hours. Weigh back challenge material. Feed with Starter diet. 16Select 2 birds/pen for NE lesion scoring, Cp counts 18 and cecacollection. Weigh birds (pen basis) and weigh back feed. Switch 22 toGrower diet. Weigh birds (pen basis) and weigh back feed. Switch 28 toFinisher diet. Weigh birds (pen basis) and weigh back feed. End ofstudy. 35 Weigh, record and necropsy all mortalities throughout 0-35 thestudy. Observe birds twice daily.Treatments

The treatments described in Table 6 below are used in this study, with12 pens for each treatment (60 pens in total). Birds are fed starter(days 0-21), grower (days 21-28) and finisher (days 28-35) diets basedon average US nutrient levels.

TABLE 6 Description of dietary treatments Treatment Description 1Challenged control: no additives 2 Challenged control: BMD 3 Challenge:Gluco-oligosaccharide

BMD® 110G (bacitracin premix; Alpharma Canada Corporation) used intreatment 2 is a feed medication premix approved for use in broilerchickens in Canada. It contains 110 g of bacitracin methylenedisalicylate per kg of premix. 0.5 kg of premix per tonne of feedprovides 55 mg of bacitracin methylene disalicylate per kg of feed.

The gluco-oligosaccharide of treatment 3 is prepared according to theprotocols described in the Examples above (e.g., Example 11). Thegluco-oligosaccharide is in liquid form with a concentration of 0.65 kgdry oligosaccharide per kg of syrup and a density of 1.28 g/mL.Inclusion rate will be 500 g of dry oligosaccharide (equivalently 600 mLof syrup or 770 grams of syrup) per tonne of feed as described in thisstudy.

Study Design

The study is conducted as a completely randomized block design. Thereare 12 blocks of pens in each block, each containing 15 male broilerchicks per pen (900 chicks in total). Treatments are randomly assignedto each pen within each block as per facility procedures.

Bird Selection/Identification

A commercial strain of male broiler chicks are obtained from a localcommercial hatchery. Fifteen male broiler chicks re placed in each penproviding an approximate stocking density of 0.6 square feet per bird atthe time of placement. Birds re weighed when they are removed from eachpen. All birds are evaluated and only chicks that are in good physicalconditions are placed in pens. Birds that die or are culled are notreplaced.

Bird Management

Birds are fed commercial broiler starter, grower and finisher diets. Alldiets are supplemented with Saccox (0.5 kg/MT) as anticoccidialmedication, and no in-feed antibiotics are used except for treatment 2which will receive BMD. Birds will not be treated for any diseases thatmay occur during the study.

Necrotic Enteritis Challenge Model

A moderately virulent strain of Clostridium perfringens (Cp; NCP-1) isused in the study. An inoculum containing approximately 10⁸ colonyforming units (CFUs) of Cp per ml is produced. Feed is removed from allpens on day 15 in the morning by raising the feeders for about 8 hours.Birds are weighed (pen basis) and counted and feed in each pen isweighed back. About 8 hours later after the start of the feedwithdrawal, challenge materials (a mixture of bacterial broth andnon-medicated starter feed at the ratio of 1 kg broth: 0.666 kg feed ina tray) is put in pens for approximately 16 hr. Water (instead ofbacterial broth) is used to make the mixture for birds in thenon-challenged control group. Five trays containing the mixture are usedin each pen.

On morning of day 16, the challenge materials are removed from the pens.Birds are fed with respective starter diets as indicated in Table 6above. The remainder of challenge materials from each pen are weighedand disposed.

A 2 ml sample of inoculum is collected from each jug at the time thatjugs are removed from the incubator using aseptic technique. The samplesare analyzed for Cp count (CFU of Cp per ml of inoculum). After thesampling and prior to issuing of challenge materials, all jugs arepoured into a container and then it is issued to respective pens.

On day 18 of the study, two (2) birds are randomly selected from eachpen, tagged, weighed, euthanized, sacrificed and ileal contents arecollected for Cp counts and cecal contents collected for microbiotasequencing. The content from the Meckel's diverticulum to the ileocecaljunction are collected into a container from each bird and labelled withbird and treatment number for Cp counts. The containers are placed in acooler containing ice pack and sent to the lab as soon as possible(i.e., on the same day). For microbiota sampling cecal contents arecollected into individual containers for each bird, labelled with birdand treatment and frozen at −70° C. until shipment to a laboratory fortesting. The entire intestinal tract is examined and scored for NElesions by a veterinarian according to the following assessment criteria(Prescott et al., 1978):

-   -   0=no gross lesions    -   1=thin-walled or friable small intestine    -   2=focal necrosis or ulceration    -   3=larger patches of necrosis    -   4=severe, extensive necrosis

All mortalities occurring throughout the study are necropsied. Birdsthat die before day 15 are not included in NE-related mortality,however, they are included in total mortality calculations. Anymortality that occurs after day 15 and has a NE lesion score of 1 orhigher are considered as NE mortality.

Assessment of Effectiveness

The following variables are measured:

-   -   Pen body weight on days 0, 15, 22, 28 and 35.        -   Average daily gain, average daily feed intake, and feed            conversion ratio for days 0 to 15, 15 to 22, 22 to 28, 28 to            35, and 0 to 35.        -   Mortality rate for 0 to 15, 15 to 22, 22 to 28, 28 to 35,            and 0 to 35.        -   Intestinal lesion scores.        -   NE related mortality 15-35.

The following variables are calculated as follows:

-   -   Body weight gain (g/d): [(Weight of all birds remaining at end        of period+weight of all birds removed during the period)−Pen        weight at start of period]/number of bird days in the period    -   Feed intake (g/d): [(Feed remaining in pen at start of        period+total feed addition weight)−feed weigh back weight at end        of period]/number of bird days in the period    -   Number of bird days=sum of bird count for each day (taken at the        beginning of the day) for all days in the period

Statistical Analysis

The study is a completely randomized block design. Pen is theexperimental unit. Block and treatment are random and fixed effects,respectively. Statistical analysis is done using the Mixed procedure ofSAS (SAS Institute Inc., Cary, N.C., USA). Where treatment effect issignificant (P≤0.05), a multiple comparison test is used to comparetreatments means.

Example 33 Growth Performance Study in Necrotic Enteritis ChallengeModel in Broiler Chickens

This study evaluated the impact of gluco-oligosaccharides preparedaccording to the protocols described in the Examples above (e.g.,Example 11), in a necrotic enteritis challenge model in broilerchickens. The effects of dietary supplementation ofgluco-oligosaccharides with and without an alternative feeding programin a necrotic enteritis challenge model were evaluated.

The schedule of events for this study was performed as set forth inTable 7 below.

TABLE 7 Schedule of events Activity Study Day Assign newly hatched malebroiler chicks to specific 0 treatment pens (15 chicks/pen) Weigh birds(pen basis) and weigh back feed. Raise 15 the feeder in each pen in theAM (no access to feed). Feed with challenge material after approximately8 hours. Weigh back challenge material. Feed with Starter diet. 16Select 2 birds/pen for NE lesion scoring, Cp counts 18 and cecacollection. Weigh birds (pen basis) and weigh back feed. Switch 22 toGrower diet. Weigh birds (pen basis) and weigh back feed. Switch 28 toFinisher diet. Weigh birds (pen basis) and weigh back feed. End ofstudy. 35 Weigh, record and necropsy all mortalities throughout 0-35 thestudy. Observe birds twice daily.Treatments

The treatments described in Table 8 below were used in this study, with12 pens for each treatment (60 pens in total). Birds were fed starter(days 0-21), grower (days 21-28) and finisher (days 28-35) diets basedon average US nutrient levels.

TABLE 8 Description of dietary treatments Treatment Description 1Challenged negative control: no additives 2 Challenged positive control:BMD 3 Challenged: Gluco-oligosaccharide

BMD® 110G (bacitracin premix; Alpharma Canada Corporation) used intreatment 2 is a feed medication premix approved for use in broilerchickens in Canada. It contains 110 g of bacitracin methylenedisalicylate per kg of premix. 0.5 kg of premix per tonne of feedprovided 55 mg of bacitracin methylene disalicylate per kg of feed.

The gluco-oligosaccharide of treatment 3 was prepared according to theprotocols described in the Examples above (e.g., Example 11). Thegluco-oligosaccharide was provided in liquid form with a concentrationof 0.65 kg dry oligosaccharide per kg of syrup and a density of 1.28g/mL. The inclusion rate was 500 g of dry oligosaccharide (equivalently600 mL of syrup or 770 grams of syrup) per tonne of feed as described inthis study.

Study Design

The study was conducted as a completely randomized block design. Therewere 12 blocks of pens in each block, each containing 15 male broilerchicks per pen (900 chicks in total). Treatments were randomly assignedto each pen within each block as per facility procedures.

Bird Selection/Identification

A commercial strain of male broiler chicks were obtained from a localcommercial hatchery. Fifteen male broiler chicks were placed in each penproviding an approximate stocking density of 0.6 square feet per bird atthe time of placement. Birds were weighed when they were removed fromeach pen. All birds were evaluated and only chicks that were in goodphysical conditions were placed in pens. Birds that died or were culledwere not replaced.

Bird Management

Birds were fed commercial broiler starter, grower and finisher diets.All diets were supplemented with Saccox (0.5 kg/MT) as anticoccidialmedication, and no in-feed antibiotics were used except for treatment 2which received BMD. Birds were not treated for any diseases that mighthave occured during the study.

Necrotic Enteritis Challenge Model

A moderately virulent strain of Clostridium perfringens (Cp; NCP-1) wasused in the study. An inoculum containing approximately 10⁸ colonyforming units (CFUs) of Cp per ml was produced. Feed was removed fromall pens on day 15 in the morning by raising the feeders for about 8hours. Birds were weighed (pen basis) and counted and the feed in eachpen was weighed back. About 8 hours after the start of the feedwithdrawal, challenge materials (a mixture of bacterial broth andnon-medicated starter feed at the ratio of 1 kg broth: 0.666 kg feed ina tray) were put in pens for approximately 16 hr. Water (instead ofbacterial broth) was used to make the mixture for birds in thenon-challenged control group. Five trays containing the mixture wereused in each pen.

On the morning of day 16, the challenge materials were removed from thepens. Birds were fed with respective starter diets as indicated in Table6 above. The remainder of challenge materials from each pen were weighedand disposed.

A 2 ml sample of inoculum was collected from each jug at the time thatthe jugs were removed from the incubator using aseptic technique. Thesamples were analyzed for Cp count (CFU of Cp per ml of inoculum). Afterthe sampling and prior to issuing of challenge materials, all jugs werepoured into a container and then it was issued to respective pens.

On day 18 of the study, two (2) birds were randomly selected from eachpen, tagged, weighed, euthanized, sacrificed and ileal contents werecollected for Cp counts and cecal contents were collected for microbiotasequencing. The content from the Meckel's diverticulum to the ileocecaljunction were collected into a container from each bird and werelabelled with bird and treatment number for Cp counts. The containerswere placed in a cooler containing ice and sent to the lab as soon aspossible (i.e., on the same day). For microbiota sampling cecal contentswere collected into individual containers for each bird, labelled withbird and treatment and frozen at −70° C. until shipment to a laboratoryfor testing. The entire intestinal tract was examined and scored for NElesions by a veterinarian according to the following assessment criteria(Prescott et al., 1978):

-   -   0=no gross lesions    -   1=thin-walled or friable small intestine    -   2=focal necrosis or ulceration    -   3=larger patches of necrosis    -   4=severe, extensive necrosis

All mortalities occurring throughout the study were necropsied. Birdsthat died before day 15 were not included in NE-related mortality,however, they were included in total mortality calculations. Anymortality that occured after day 15 and had a NE lesion score of 1 orhigher were considered as NE mortality.

Assessment of Effectiveness

The following variables were measured:

-   -   Pen body weight on days 0, 15, 22, 28 and 35.        -   Average daily gain, average daily feed intake, and feed            conversion ratio for days 0 to 15, 15 to 22, 22 to 28, 28 to            35, and 0 to 35.        -   Mortality rate for 0 to 15, 15 to 22, 22 to 28, 28 to 35,            and 0 to 35.        -   Intestinal lesion scores.        -   NE related mortality 15-35.

The following variables were calculated as follows:

-   -   Body weight gain (g/d): [(Weight of all birds remaining at end        of period+weight of all birds removed during the period)−Pen        weight at start of period]/number of bird days in the period    -   Feed intake (g/d): [(Feed remaining in pen at start of        period+total feed addition weight)−feed weigh back weight at end        of period]/number of bird days in the period    -   Number of bird days=sum of bird count for each day (taken at the        beginning of the day) for all days in the period

Statistical Analysis

The study was a completely randomized block design. Pen was theexperimental unit. Block and treatment were random and fixed effects,respectively. Statistical analysis was done using the Mixed procedure ofSAS (SAS Institute Inc., Cary, N.C., USA). Where treatment effect wassignificant (P≤0.05), a multiple comparison test was used to comparetreatments means.

Results

Day 35 body weights were determined to be 2.380 kg for BMD treated dietsand 2.375 kg for the gluco-oligosaccharide diets, which werestatistically indistinguishable to p<0.04. Therefore, thegluco-oligosaccharide was as effective as the antibiotic treatment inmaintaining body weight in the presence of the disease challenge.Similarly, the average daily feed intake (ADFI) of birds fed thegluco-oligosaccharide was 96.5 g/day, which was statisticallyindistinguishable from the 96.8 g/day consumed by birds fed theantibiotic.

Bacterial enumeration indicated that birds fed the gluco-oligosaccharideexhibited a lower number of Cp organisms than the negative control, with4.31 cfu/g for birds fed the gluco-oligosaccharide versus 5.40 cgu/g forthe negative control.

Example 34 Determining the Effects of Oligosaccharide on GrowthPerformance of Nursery Pigs

This Example will be conducted to determine the effects ofoligosaccharide level in diets with or without growth promoting levelsof trace minerals and antibiotics on growth performance of nursery pigs.

Procedures

Pigs: Approximately 3,240 pigs will be placed in three rooms at anursery farm with 27 pigs per pen and 15 pens per treatment in arandomized complete block design (a total of 8 treatments across 40 pensin each of 3 rooms). All pens will be balanced with 14 gilts and 13barrows. At weaning, weight, age and sow farm source will be recorded.At weaning, pigs will be placed with the same number of pigs from eachsow farm per pen.

Allotment: Prior to allotment and each weighing event, standard weightswill be put on each corner of the scale will ensure that the scale ismeasuring weights correctly. At placement, the average weight of thepigs in each pen will be determined and data provided as soon aspossible for treatment allotment. At weaning, pens will be ranked byaverage weight and weight blocks and pens assigned to the rankedweights. Treatments will then be randomly assigned within weight blocks.When the treatment assignments are done, pen assignments will beprovided also as soon as possible so dietary treatments information canbe entered into the feeding system and pigs can fed. Pigs will have freeaccess to feed and water at all moments of the trial.

Schedule: At arrival, pigs will be allotted to pens. A common pelleteddiet will be fed to all pigs for 7 days. This diet will contain 55 ppmof Mecadox (50 g/ton). Dietary treatments will be fed from day 7 to theend of the nursery phase (approximately 55 lb). Pens will be allotted todietary treatments on day 7. Diets will be fed in two phases with thefirst phase from day 7 to 21 after weaning and the second phase from day21 to the end of the nursery phase (day 21 to 42 after weaning).

Treatments: Dietary treatments will be randomly assigned to 40 pens ineach of 3 rooms for 5 replications per room and 15 replications total.The 8 treatments are structured as a 2×4 factorial with two diet types(with and without antibiotic; 55 ppm of Mecadox) and four levels ofgluco-oligosaccharide (0, 200, 400 or 600 ppm). Thegluco-oligosaccharides are prepared according to the procedures setforth in Examples above. The gluco-oligosaccharides will be provided ona dry carrier such that the 600 ppm will be in a 0.25% final dietinclusion rate (5 lb/ton). All diets will contain the same growthpromoting levels of Cu and Zn at 200 ppm Cu and 2,000 ppm Zn, in thephase 2 diets and 200 ppm Cu in the phase 3 diet. The diets containing 0and 0.25% of the premix containing the gluco-oligosaccharides will beblended to form the intermediate treatments.

Diet Preparation: Diets will be fed in meal form. The four dietsrequired will be the control diets for each diet type and the dietscontaining 0.25% gluco-oligosaccharide premix. The actualoligosaccharide levels in the test will be 0, 200, 400, and 600 ppm witha carrier used such that the premix at 0.25% (5 lb/ton) will provide0.45% oligosaccharide. Treatments will be equally spaced with thecontrol and 0.25% diets blended as set forth in Table 9 below.

TABLE 9 Ratio of control:0.25% diet to form each treatment Premix:Control 0.083% 0.167% 0.25% Oligosaccharide, ppm: 0 200 400 600Control:0.25% 100:0 66.7:33.3 33.3:66.7 0:100

A gallon sample bag full of each diet will be collected from the feedsystem as diet is being dispensed 3 days after beginning feeding of eachtreatment and 3 days before the end of each phase and kept refrigerateduntil the end of the experiment when all samples will be forwarded tothe swine lab for analysis and storage. Samples will be labeled withdate, diet, and trial number. Complete diet samples will be sent forproximate analysis and analysis of gluco-oligosaccharide level.

Live Animal Data Collection: Pigs will be weighed, counted and feeddisappearance determined every 7 days during the experiment. Prior toeach weighing event standard weights will be put on each corner of thescale will ensure that the scale is measuring weights correctly. Piginventory, weight, removal and feed intake data will be recorded andmaintained throughout the trial. Data will be collected on the standarddata collection spreadsheet.

Removals: For pigs that die or must be treated or removed from the studyfor any reason, the date and weight will be recorded as soon as theyoccur. This will be accompanied with notes on the suspected cause ofdeath or reason for removal. If any pig is treated with medication, thedate, reason for treatment and medication used will be recorded.

Statistical analysis: Pens will be randomly allotted to treatments usingbody weight as a blocking factor. Weight block will be added to themodel as a random effect. Main effects and interaction between diet typeand gluco-oligosaccharide level will be determined. Data will also beanalyzed for linear and quadratic effect of gluco-oligosaccharidelevels. The experimental data will be analyzed using a statisticalanalysis tools.

Example 35 Determining the Effects of Oligosaccharide on GrowthPerformance of Nursery Pigs

This Example was conducted to determine the effects of oligosaccharidelevel in diets with or without growth promoting levels of trace mineralsand antibiotics on growth performance of nursery pigs.

Procedures

Pigs: Approximately 3,240 pigs were placed in three rooms at a nurseryfarm with 27 pigs per pen and 15 pens per treatment using a randomizedcomplete block design (a total of 8 treatments across 40 pens in each of3 rooms). All pens were balanced with 14 gilts and 13 barrows. Atweaning, weight, age and sow farm source were recorded. At weaning, pigswere placed with the same number of pigs from each sow farm per pen.

Allotment: Prior to allotment and each weighing event, standard weightswere placed on each corner of the scale to ensure that the scale wascorrectly calibrated. At placement, the average weight of the pigs ineach pen were determined and the data was provided as soon as possiblefor treatment allotment. At weaning, pens were ranked by average weightand weight blocks and pens were assigned to the ranked weights.Treatments were then randomly assigned within weight blocks. When thetreatment assignments were done, pen assignments were provided also assoon as possible, and dietary treatments information was entered intothe feeding system. Pigs were granted free access to feed and waterthroughout the trial.

Schedule: At arrival, the pigs were allotted to pens. A common pelleteddiet was fed to all pigs for 7 days. This diet contained 55 ppm ofMecadox (50 g/ton). Dietary treatments were fed from day 7 to the end ofthe nursery phase (approximately 55 lb). Pens were allotted to dietarytreatments on day 7. Diets were fed in two phases with the first phasefrom day 7 to 21 after weaning and the second phase from day 21 to theend of the nursery phase (day 21 to 42 after weaning).

Treatments: Dietary treatments were randomly assigned to 40 pens in eachof 3 rooms for 5 replications per room and 15 replications total. The 8treatments were structured as a 2×4 factorial with two diet types (withand without antibiotic; 55 ppm of Mecadox) and four levels ofgluco-oligosaccharide (0, 200, 400 or 600 ppm). Thegluco-oligosaccharides were prepared according to the procedures setforth in Examples above. The gluco-oligosaccharides were provided on acorn meal carrier, as described in Example 18, such that the 600 ppmdose was obtained with a 0.25% final diet inclusion rate (5 lb premixper ton final feed). All diets contained the same growth promotinglevels of Cu and Zn at 200 ppm Cu and 2,000 ppm Zn, in the phase 2 dietsand 200 ppm Cu in the phase 3 diet. The diets containing 0 and 0.25% ofthe premix containing the gluco-oligosaccharides were blended to formthe intermediate treatments.

Diet Preparation: Diets were fed in meal form. The four diets requiredwere the control diets for each diet type and the diets containing 0.25%gluco-oligosaccharide premix. The actual oligosaccharide levels in thetest were 0, 200, 400, and 600 ppm with a carrier used such that thepremix at 0.25% (5 lb/ton) will provide 600 ppm oligosaccharide.Treatments were equally spaced with the control and 0.25% diets blendedas set forth in Table 10 below.

TABLE 10 Ratio of control:0.25% diet to form each treatment Premix:Control 0.083% 0.167% 0.25% Oligosaccharide, ppm: 0 200 400 600Control:0.25% 100:0 66.7:33.3 33.3:66.7 0:100

A gallon sample bag full of each diet was collected from the feed systemas the diet was dispensed 3 days after beginning feeding of eachtreatment and 3 days before the end of each phase and kept refrigerateduntil the end of the experiment when all samples were forwarded to theswine lab for analysis and storage. Samples were labeled with date,diet, and trial number. Complete diet samples were sent for proximateanalysis and analysis of gluco-oligosaccharide level.

Live Animal Data Collection: Pigs were weighed, counted and feeddisappearance determined every 7 days during the experiment. Prior toeach weighing event standard weights were placed on each corner of thescale to ensure proper calibration of the scale. Pig inventory, weight,removal and feed intake data were recorded and maintained throughout thetrial. Data were collected on the standard data collection spreadsheet.

Removals: For pigs that died, required treatment, or were removed fromthe study for any reason, the date and weight of the corresponding pigwere recorded as soon as they occur. This record was accompanied withnotes on the suspected cause of death or reason for removal. If any pigwas treated with medication, the date, reason for treatment andmedication used was recorded.

Statistical analysis: Pens were randomly allotted to treatments usingbody weight as a blocking factor. Weight block was added to the model asa random effect. Main effects and interaction between diet type andgluco-oligosaccharide level were determined. Data was analyzed forlinear and quadratic effect of gluco-oligosaccharide levels.

Results

Average values of the 0-42d Body Weight Gain (BWG), 0-42d Average DailyGain (ADG), 0-42d Average Daily Feed Intake (ADFI), and 0-42d FeedConversion Ratio (FCR) for nursary pigs fed control and treated dietswere determined to be as summarized in Table 11 below.

TABLE 11 Anti- Negative Negative Negative Anti- Positive PostitivePositive biotic Control + Control + Contorl + biotic Control + Control +Control Negative Oligo Oligo Oligo Positive Oligo Oligo Oligo ControlDose 1 Dose 2 Dose 3 Control Dose 1 Dose 2 Dose 3 Mecadox, ppm 0 0 0 055 55 55 55 Oligo, ppm 0 200 400 600 0 200 400 600 BWG, lbs 39.98 39.7240.52 40.68 40.69 42.31 42.15 43.22 ADG, lbs/day 0.91 0.92 0.93 0.930.93 0.98 0.96 1.00 ADFI, lbs/day 1.35 1.34 1.37 1.36 1.37 1.42 1.411.43 FCR, lbs/lbs 1.47 1.46 1.47 1.46 1.47 1.46 1.46 1.43

Statistical variation and the effect of increasing dose of thegluco-oligosaccharide was determined by linear regression analysis, asillustrated by FIGS. 1, 2, 3 and 4 . Error bars in the figures denotethe standard error in the mean (SEM), and the dotted lines indicate theresulting linear regression analyses. See FIGS. 20-23 .

The BWG benefit, ADG benefit, ADFI benefit, and FCR benefit werecalculated for 0-42 days by taking the ratio of the respective valueswith respect to their corresponding controls and performing linearregression to determine the dose-effect of the gluco-oligosaccharide,resulting in the following regression equations set forth in Table 12below.

TABLE 12 Antibiotic Negative Antibiotic Positive Control plus Controlplus Gluco-Oligosaccharide Gluco-Oligosaccharide Inter- Inter- cept,Slope, cept, Slope, % %/ppm p-value % %/ppm p-value BWG 0.0% 2.61E−05 p< 0.10 2.5% 9.29E−05 p < 0.10 Benefit ADG 0.0% 4.32E−05 p < 0.01 3.2%1.04E−04 p < 0.20 Benefit ADFI 0.0% 1.59E−05 p < 0.20 2.4% 6.30E−05 p <0.20 Benefit FCR 0.0% 4.86E−06 p < 0.15 −0.2%  4.08E−05 p < 0.10 Benefit

The regression equations were used to determine the BWG, ADG, ADFI, andFCR benefit provided by 600 ppm gluco-oligosaccharide, both in thepresence and absence of the antibiotic growth promoter as set forth inTable 13 below.

TABLE 13 ABX ABX Negative ABX Positive Positive Control + 600 ppmControl + 600 ppm Control gluco-oligosaccharide gluco-oligosaccharideBWG Benefit 2.5% 1.6% 8.1% ADG Benefit 3.2% 2.6% 9.5% ADFI Benefit 2.4%1.0% 6.1% FCR Benefit −0.2% 0.3% 2.2%

As expected, addition of the antibiotic growth promoter Mecadox (ABXPositive Control) resulted in an improved 0-42d BWG of 2.5%, andimproved 0-42d ADG of 3.2%, and an improved 0-42d ADGI of 2.4%. Also asexpected, the addition of the antibiotic growth promoter did not improvethe 0-42d FCR.

As apparent from the positive slope of the linear regressions, additionof the gluco-oligosaccharide provided a positive benefit in the 0-42dBWG, 0-42d ADG, 0-42d ADGI, and 0-42d FCR. At a particular dose of 600ppm, addition of the gluco-oligosaccharide resulted in an improved 0-42dBWG of 1.6%, statistically comparable to that of the antibiotic, animproved 0-42d ADG of 2.6%, statistically comparable to the antibiotic,and an improved 0-42d ADGI of 1.0%, statistically comparable to theantibiotic. Furthermore, the addition of the gluco-oligosaccharideresulted in an improved FCR, in contrast to the antibiotic.

Surprisingly, the combination of the antibiotic and thegluco-oligosaccharide provided a significant improvement in the livegrowth performance, greater than that obtained with either thegluco-oligosaccharide or antibiotic alone, or the sum of theirindividual contributions.

What is claimed is:
 1. An animal feed pre-mix, comprising: a carrier material; and (ii) a gluco-oligosaccharide composition with a weight average molecular weight between 1000 g/mol and 2000 g/mol, wherein the carrier material has less than 50 ppm by weight of an antibiotic selected from the group consisting of bacitracin, bacitracin methylene disalicylate, bacitracin-zinc, virginiamycin, bambermycin, avilamycin, and efrotomycin, or any combination thereof.
 2. The animal feed pre-mix of claim 1, wherein at least 10 wt % dry gluco-oligosaccharide composition is present in the animal feed pre-mix.
 3. The animal feed pre-mix of claim 1, wherein the carrier material is selected from the group consisting of ground rice hulls, ground oat hulls, feed grade silica gel, feed grade fumed silica, corn gluten feed, corn gluten meal, dried distiller's grains, clay, vermiculite, diatomaceous earth, milled corn, and combinations of distinct carrier materials recited herein.
 4. The animal feed pre-mix of claim 1, wherein at least 50 dry wt % of the gluco-oligosaccharide composition has a degree of polymerization of at least
 3. 5. The animal feed pre-mix of claim 1, wherein the animal feed is poultry feed.
 6. The animal feed pre-mix of claim 5, wherein the poultry feed: (i) reduces feed conversion ratio (FCR) by between 1 to 10%; or (ii) increases average daily weight gain by between 1 to 10%; or (iii) increases average daily feed intake by between 1 to 10%; or any combination of (i)-(iii), when fed to poultry as compared to poultry fed a feed composition without the gluco-oligosaccharide composition.
 7. The animal feed pre-mix of claim 1, wherein the animal feed is swine feed.
 8. The animal feed pre-mix of claim 7, wherein the swine feed: (i) reduces feed conversion ratio (FCR) by between 1 to 15%; or (ii) increases average daily weight gain by between 1 to 15%; or (iii) increases average daily feed intake by between 1 to 15%; or any combination of (i)-(iii), when fed to swine as compared to swine fed a feed composition without the gluco-oligosaccharide composition.
 9. The animal feed pre-mix of claim 1, wherein the gluco-oligosaccharide composition is a functionalized gluco-oligosaccharide composition comprising a pendant functional group selected from the group consisting of glucosamine, galactosamine, lactic acid, acetic acid, citric acid, pyruvic acid, succinic acid, glutamic acid, aspartic acid, glucuronic acid, itaconic acid, malic acid, maleic acid, adipic acid, sorbitol, xylitol, arabitol, glycerol, erythritol, mannitol, galacitol, fucitol, iditol, inositol, volemitol, lacitol, propanediol, butanediol, pentanediol, sulfate and phosphate.
 10. An animal feed composition, comprising (i) a base feed in addition to (ii) the animal feed pre-mix of claim
 1. 11. The animal feed pre-mix of claim 1, wherein the moisture content of the animal feed pre-mix is less than 20 wt %.
 12. The animal feed pre-mix of claim 1, wherein at least 10 dry wt % of the gluco-oligosaccharide composition has a degree of polymerization of at least
 3. 13. The animal feed pre-mix of claim 1, wherein the animal feed pre-mix is in a dry, flowable powder form.
 14. The animal feed pre-mix of claim 1, wherein the gluco-oligosaccharide composition is a syrup.
 15. The animal feed pre-mix of claim 14, wherein the syrup has a solids content of at least 60 wt % 60%.
 16. The animal feed pre-mix of claim 1, wherein less than 50 ppm of an antibiotic is present in the animal feed pre-mix.
 17. The animal feed pre-mix of claim 1, wherein the carrier material comprises less than 50 ppm of coccidiostat.
 18. The animal feed composition of claim 10, wherein the animal feed composition further comprises vitamins.
 19. The animal feed composition of claim 10, wherein the animal feed composition further comprises essential amino acids.
 20. The animal feed composition of claim 10, wherein the base feed is fodder, corn-soy based diet, wheat-soy based diet, grass, grain, legumes, hay, stover, straw, silage, wheat, barley, maize, sorghum, rye, oats, triticale, rice, soybeans, peas, seaweed, yeast, molasses, lactose, milk, milk solids, chicken meal, fish meal, bone meal, blood, or a combination of distinct base feeds recited herein.
 21. The animal feed composition of claim 10, wherein less than 50 ppm of coccidiostat is present in the animal feed composition. 